Acyclic and cyclic guanidine- and acetamidine derivatives, their preparation and their use as pesticides, ESP as parasiticides

ABSTRACT

Novel pesticides of formula (I)                    
     wherein the substituents, R, R 1 , R 2 , R 2 ′, T, U, X and Y are as defined in claim 1, are described. Also described are compositions suitable for use as parasiticides comprising those compounds as active ingredient and to methods of controlling parasites that are based on the administration of those compounds or compositions, and to the use of the said compounds and compositions in a method of controlling parasites and in the manufacture of pesticides for use against parasites. Also described are intermediates of formula (XX)                    
     wherein 
     R 1 , R 2 , R 2 ′, T, U, X and Y are as defined in claim 1; and 
     Hal is halogen. 
     The latter also exhibit parasiticidal activity and are suitable for the preparation of the compounds of formula (I).

This application is a division of application Ser. No. 09/850,378. filedMay 7, 2001 now U.S. Pat. No. 6,538,013, which is a continuation-in-partof PCT Patent Application No. PCT/EP99/008765, filed Nov. 15, 1999,which applications are herein incorporated by reference.

The present invention relates to novel pesticides of the formula (I)below having improved action against parasites; to compositions suitablefor use as parasiticides comprising those compounds as active ingredientand to methods of controlling parasites that are based on theadministration of those compounds or compositions, and to the use of thesaid compounds and compositions in a method of controlling parasites andin the manufacture of pesticides for use against parasites. Alsodescribed are intermediates of formula (XX) which themselves haveparasiticidal activity and are excellently suitable for the preparationof compounds of formula (I).

Numerous pesticides are known that can be used in controlling parasiteson warm-blooded animals. The control is effected principally by twodifferent methods; either by way of contact action by topical andtherefore external treatment of the host animal or systemically, that isto say by oral, transdermal or percutaneous administration to the hostanimal and ingestion of the active ingredient by the parasites via theblood of the host animal.

Far fewer substances are available for systemic use than for topicalapplication, because only substances that have a systemic action and arewell tolerated by the host animal can be used.

Compounds having as characteristic structural element the sub-structureof formula (II):

wherein R₁, X, Y, T and U are as defined for formula (I) hereinbelow,form a very interesting class of substances on account of theirpronounced topical and systemic action.

A prominent individual example is nitenpyram, a compound of formula(III)

Nitenpyram and other examples of this class of substances are disclosed,together with their preparation, in EP 0 302 389. Those compounds aredescribed as pesticides having very pronounced insecticidal activity.Further examples of this class of substances are, for example, thesubjects of the following patent applications: European publishedspecifications Nos. 285 985, 302 833, 376 279, 471 372, 364 844, 493369, 381 130, 529 680, 163 855, 375 907, 259 738, 386 565, 383 091 and590 425; U.S. Pat. Nos. 5,063,236, 5,302,605 and 4,742,060; and alsoDE-4 207 604; GB-2 228 003 and WO 93/24002. Certain substituted4-nitroimino-perhydro-1.3.5-oxadiazine derivatives and their use aspesticides and intermediates are described in WO 98/06710.

Nitenpyram and other examples of this class of substances that have thesaid structural element of formula (II) are extremely effective whenadministered as contact pesticides, for example externally, that is tosay topically, to an infested host animal where they come into directcontact with the parasites. They also, however, exhibit a good systemicimmediate action when they are administered to the infested host animalorally, parenterally, via injection or via implant.

The action, which is pronounced per se, has a serious disadvantage,however, in that it has been found that while the compounds have a highinitial action, their action falls off rapidly only a short time afteradministration. This can be observed particularly clearly after systemicadministration and can be monitored by reference to the bioavailability.Blood level measurements show that in many cases high blood levels areachieved even after a few minutes or, more rarely, after a few hours,but these levels then fall within a few hours, at best within a fewdays, and therefore fall to below an effective concentration much toorapidly.

In order to eliminate this shortcoming, numerous, but unfortunatelyunsuccessful, experiments have already been carried out. For example, ithas been shown that a prolongation of the systemic action by increasingthe dose can be achieved only to a limited extent. If, for example,depots sufficiently large for the active ingredient to be released overseveral weeks were to be placed under the skin or in the muscles, thenthe amounts to be injected or implanted would have to be so large thatthey would no longer be tolerated by the host animal; local irritation,skin eruptions and painful areas develop. This solution, possible perse, therefore fails on practical and, of course, also ethical grounds.Similarly, it has been found that a long-term action is not achievableby an increased oral dose.

When the known compounds having the structural element of formula (II)are administered, it is principally observed that a major part of thesubstance exhibits its full action only over a short period of timeimmediately after administration and thereafter the action very rapidlydeclines. This has serious consequences for preparations for use inveterinary medicine, for example, for tablets, injections or fortreatment using the pour-on or spot-on method. Because of the shortduration of action it is necessary to repeat treatments at shortintervals, which means that the keeper of the animal must either repeatthe treatment himself, or have it carried out by a veterinary surgeon,at short intervals. Such an intensive treatment program requires a highdegree of discipline, however, and, as experience has shown, after onlya short time gives rise to stress on the part of the animal and on thepart of the animal's keeper, which not infrequently results in aversionto the treatment and leads to its premature discontinuation.

Prolongation of the action of this inherently extremely effective classof substances has therefore long been a desirable but apparentlyunattainable goal. The problem underlying the present invention was toachieve that goal and provide substances suitable for use as pesticideshaving significantly improved properties, especially having a pronouncedlong-term action.

By the provision of the compounds of formula (I) below it has now,surprisingly, been possible for compounds having the structural elementof formula (II) to be modified chemically in such a manner that a highdegree of long-term bioavailability after administration is achievedwithout it being necessary to accept adverse effects as a result.

The new, improved compounds are compounds of formula (I) below:

wherein

R₁ is hydrogen or a radical from the group C₁-C₄alkyl, formyl,C₁-C₆alkylcarbonyl, C₁-C₄alkylsulfonyl, aryl, arylsulfonyl,arylcarbonyl, heterocyclyl and heterocyclyl-substituted C₁-C₆alkyl,which radical is unsubstituted or mono- or poly-substituted by identicalor different substituents; the said substituents being C₁-C₄alkyl,C₁-C₄alkoxy, C₁-C₄alkylthio, C₁-C₄haloalkyl, halogen, hydroxy, cyano,nitro, amino, C₁-C₄alkylamino, C₁-C₄alkyl)₂amino, alkoxycarbonyl,C₁-C₄alkylsulfonyl and arylsulfonyl;

X is CH or N;

Y is an electron-withdrawing radical, preferably cyano, nitro orC₁-C₆haloalkyl-carbonyl, especially CO—CF₃;

T has the meanings of R₁ or together with U forms a C₁-C₄alkylene bridgewhich is unsubstituted or substituted by a radical R₁, or T and Utogether with the group —N—C—N— form a saturated or unsaturated 5- or6-membered heterocyclic ring which may in addition contain as furtherhetero atom O or S or the hetero group —N(C₁-C₆alkyl)-;

U is hydrogen or C₁-C₆alkyl, preferably hydrogen, methyl or ethyl;

R₂ is hydrogen or C₁-C₆alkyl;

R₂′ is hydrogen or C₁-C₆alkyl; and

R is C₁-C₂₀alkyl, C₂-C₂₀alkenyl, C₂-C₆alkynyl or heterocyclyl, each ofthose radicals being unsubstituted or substituted by one or moreidentical or different substituents, the said substituents beingselected from the group halogen, cyano, nitro, hydroxy, C₁-C₆alkoxy,C₁-C₆alkylthio, C₁-C₆haloalkyl, C₁-C₆haloalkoxy and phenyl; or isC₃-C₇cycloalkyl that is unsubstituted or mono- or poly-substituted byidentical or different substituents selected from halogen, cyano, nitro,hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₁-C₆alkoxy,C₁-C₆alkylthio, C₁-C₆haloalkyl, C₁-C₂₀haloalkoxy and phenyl;

wherein each phenyl moiety is itself unsubstituted or mono- orpoly-substituted by identical or different substituents selected fromhalogen, cyano, nitro, hydroxy, C₁-C₆alkyl, C₁-C₆alkoxy, C₁-C₆alkylthio,C₁-C₆haloalkyl and C₁-C₂₀haloalkoxy; or

is phenyl phenoxyphenyl each of which is unsubstituted or mono- orpoly-substituted by identical or different substituents selected fromhalogen, cyano, nitro, hydroxy, C₁-C₆alkyl, C₁-C₆alkoxy, C₁-C₆alkylthio,C₁-C₆haloalkyl and C₁-C₂₀haloalkoxy.

Within the scope of formula (I) above, preference is given to compounds,wherein R is C₁-C₂₀alkyl, C₂-C₂₀alkenyl or C₂-C₆alkynyl, each of thoseradicals being unsubstituted or mono- or poly-substituted by identicalor different substituents, the said substituents being selected from thegroup halogen, cyano, nitro, hydroxy, C₁-C₆alkoxy, C₁-C₆alkylthio,C₁-C₆haloalkyl, C₁-C₆haloalkoxy and phenyl; or is C₃-C₇cycloalkyl thatis unsubstituted or mono- or poly-substituted by identical or differentsubstituents selected from halogen, cyano, nitro, hydroxy, C₁-C₆alkyl,C₂-C₆alkenyl, C₂-C₆alkynyl, C₁-C₆alkoxy, C₁-C₆alkylthio, C₁-C₆haloalkyl,C₁-C₂₀haloalkoxy and phenyl; or is phenyl phenoxyphenyl each of which isunsubstituted or mono- or poly-substituted by identical or differentsubstituents selected from halogen, cyano, nitro, hydroxy, C₁-C₆alkyl,C₁-C₆alkoxy, C₁-C₆alkylthio, C₁-C₆haloalkyl, C₁-C₂₀haloalkoxy.

Within the group of compounds of formula (I) wherein R isC₃-C₇cycloalkyl that is mono- or poly-substituted by identical ordifferent substituents selected from halogen, cyano, nitro, hydroxy,C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₁-C₆alkoxy, C₁-C₆alkylthio,C₁-C₆haloalkyl, C₁-C₂₀haloalkoxy and phenyl; wherein the phenyl moietyis itself unsubstituted or mono- or poly-substituted by identical ordifferent substituents selected from halogen, cyano, nitro, hydroxy,C₁-C₆alkyl, C₁-C₆alkoxy, C₁-C₆alkylthio, C₁-C₆haloalkyl andC₁-C₂₀haloalkoxy, special preference on account of their pronouncedactivity is given to those compounds in which the C₃-C₇cycloalkylradical is substituted by one substituent and in the 1-position.

By the introduction of the side chain of formula (IV):

wherein R₂, R₂ and R are as defined for formula (I), it has now beenpossible to prepare substances that exhibit simultaneously a number oflong sought and very desirable properties and are now actually suitablefor practical use:

1. The compounds of formula (I) have a high level of activity againstarthropods, especially blood-sucking insects.

2. They exhibit excellent tolerability when administered systemicallyand topically to a host animal.

3. They are distinguished by an appreciably longer duration of action incomparison with known compounds having the structural element of formula(II), which can readily be demonstrated by reference to the mortality ofthe parasites on the host animal.

4. They can be handled satisfactorily from the standpoint of formulationtechnology and have adequate storage stability.

It was not to be predicted that the chemical modification carried outhere would result in these advantageous properties and would be able toimpart to the novel compounds of formula (I) these positive long-termproperties.

In the context of the present invention, the definitions of thesubstituents are to be understood as follows: each of the substituentsindicated under formula (I) that can itself be poly-substituted issubstituted by either identical or different substituents, that is tosay multiple substitutions are to be interpreted as meaning thatidentical or different substituents can be present simultaneously on thesame radical. For example, a radical poly-substituted by halogen mayhave either several identical halogen atoms or several different halogenatoms. Multiple substitutions are to be interpreted accordingly forother radicals.

The alkyl groups appearing in the definitions of substituents in terms,such as alkyl, alkylcarbonyl, alkylsulfonyl, alkoxy, alkylthio,haloalkyl, alkylamino, dialkylamino, haloalkylcarbonyl, etc. may,according to the number of carbon atoms, be straight-chain or branchedand are, e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl,octyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, hexadecyl, octadecylor eicosyl; and the branched isomers thereof, e.g., isopropyl, isobutyl,sec-butyl, tert-butyl, isopentyl, neopentyl or isohexyl. Alkoxy,haloalkyl, haloalkylcarbonyl and haloalkoxy radicals are derived fromthe mentioned alkyl groups and accordingly are partially or fullyhalogenated radicals; poly-halogenated radicals carry identical ordifferent halogen atoms.

The terms halo and halogen denote halogen atoms and generally denotefluorine, chlorine, bromine or iodine, here preferably fluorine orchlorine, as substituent of an alkyl group especially fluorine and assubstituent of a heterocycle especially chlorine.

Examples of haloalkyl—as a group per se and as a structural element ofother groups and compounds, such as haloalkoxy—are methyl mono- totri-substituted by fluorine, chlorine and/or bromine, such as CHF₂ orCF₃; ethyl mono- to penta-substituted by fluorine, chlorine and/orbromine, such as CH₂CF₃, CF₂CF₃, CF₂CCl₃, CF₂CHCl₂, CF₂CHF₂, CF₂CFCl₂,CF₂CHBr₂, CF₂CHClF, CF₂CHBrF or CClFCHClF; propyl or isopropyl mono- tohepta-substituted by fluorine, chlorine and/or bromine, such asCH₂CHBrCH₂Br, CF₂CHFCF₃, CH₂CF₂CF₃ or CH(CF₃)₂; and butyl mono- tonona-substituted by fluorine, chlorine and/or bromine, or one of itsisomers, such as CF(CF₃)CHFCF₃ or CH₂(CF₂)₂CF₃.

In the context of the present invention, Het and heterocyclyl are to beunderstood as meaning aliphatic or aromatic cyclic radicals that containat least one oxygen, sulfur or nitrogen atom. Five- and six-memberedheterocycles are preferred. Heterocyclyl accordingly typically includessubstituents such as dioxolanyl, pyrrolidinyl, piperidinyl, morpholinyl,pyridyl, pyrrolyl, furyl, thienyl, imidazolyl, tetrahydrofuryl,tetrahydropyranyl, dihydrofuryl, dihydropyranyl, isoxazolyl, oxazolyl,thiazolyl, oxazolinyl, oxazolidinyl, imidazolinyl, imidazolidinyl anddioxanyl. Special preference is given to those which are unsubstitutedor contain one or two halogen atoms, halogen here being fluorine,chlorine or bromine, but especially chlorine. Of those heterocyclicradicals special mention should be made of pyridyl, thiazolyl andtetrahydrofuryl. More especially preferred sub-groups of formula (I)contain as heterocyclyl radicals 5,6-dichloro-pyridin-3-yl,6-chloro-pyridin-3-yl, 2-chlorothiazol-5-yl and tetrahydrofuran-3-yl.

Aryl by itself or as part of a substituent, e.g., arylsulfonyl,arylcarbonyl or aralkyl, is phenyl or naphthyl, preferably phenyl.

Alkenyl is, in each case giving due consideration to the number ofcarbon atoms contained in the group in question, either straight-chain,e.g., vinyl, 1-methylvinyl, allyl, 1-butenyl or 2-hexenyl; or branched,e.g., isopropenyl. Alkynyl is, in each case giving due consideration tothe number of carbon atoms contained in the group in question, eitherstraight-chain, e.g., propargyl, 2-butynyl or 5-hexynyl, or branched,e.g., 2-ethynylpropyl or 2-propargylisopropyl. C₃-C₇Cycloalkyl iscyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl.

Typical C₁-C₄alkylene bridges are —CH₂—, —CH₂—CH₂—, —CH₂—CH₂—CH₂—,—CH₂—CH₂—CH₂—CH₂—, —CH(CH₃)—CH₂—, —CH(C₂H₅)—CH₂—, —CH₂—CH(CH₃)—CH₂—,—CH(CH₃)—CH(CH₃)—, —C(CH₃)₂—, —C(CH₃)(C₂H₅)— and —C(C₂H₅)₂—.

Compounds of formula (I) having at least one basic centre may form acidaddition salts with strong acids. Physiologically tolerable acidaddition salts are of special interest.

An interesting sub-group within the compounds according to the inventionis formed by compounds of formula (I) wherein

Y is NO₂;

R₁ is hydrogen or a radical from the group C₁-C₄alkyl, formyl,C₁-C₆alkylcarbonyl, C₁-C₄alkylsulfonyl, aryl, arylsulfonyl,arylcarbonyl, heterocyclyl and heterocyclyl-substituted C₁-C₆alkyl,which radical is unsubstituted or mono- or poly-substituted by identicalor different substituents; the said substituents being C₁-C₄alkyl,C₁-C₄alkoxy, C₁-C₄alkylthio, C₁-C₄haloalkyl, halogen, hydroxy, cyano,nitro, amino, C₁-C₄alkylamino, C₁-C₄alkyl₂amino, alkoxycarbonyl,C₁-C₄alkylsulfonyl and arylsulfonyl;

T has the meanings of R₁ or together with U forms a C₁-C₄alkylene bridgewhich is unsubstituted or substituted by a radical R₁, or T and Utogether with the group —N—C—N— form a saturated or unsaturated 5- or6-membered heterocyclic ring which may in addition contain as furtherhetero atom O or S or the hetero group —N(C₁-C₆alkyl)-;

U is hydrogen or C₁-C₆alkyl, preferably hydrogen, methyl or ethyl; and

R₂, R₂′ and R are as defined for formula (I).

Another interesting group is formed by compounds of formula (I): wherein

R₁ is —CH₂-Het;

X is CH;

Y is NO₂;

Het is heterocyclyl that is unsubstituted or mono- or poly-substitutedby identical or different substituents; the substituents beingC₁-C₄alkyl, C₁-C₄alkoxy, C₁-C₄alkylthio, C₁-C₄haloalkyl, halogen,hydroxy, cyano, nitro, amino, C₁-C₄alkylamino, C₁-C₄alkyl₂amino,alkoxycarbonyl, C₁-C₄alkylsulfonyl and arylsulfonyl;

T (1) is a radical from the group formyl, C₁-C₆alkylcarbonyl,C₁-C₄alkylsulfonyl, aryl, arylsulfonyl, arylcarbonyl, heterocyclyl andheterocyclyl-substituted C₁-C₆alkyl, which radical is unsubstituted ormono- or poly-substituted by identical or different substituents; thesaid substituents being C₁-C₄alkyl, C₁-C₄alkoxy, C₁-C₄haloalkyl,halogen, hydroxy, cyano, nitro, amino, C₁-C₄alkylamino,C₁-C₄alkyl₂amino, C₁-C₄alkylsulfonyl and arylsulfonyl; or

(2) T together with U forms a C₁-C₄alkylene bridge which isunsubstituted or substituted by a radical selected from the groupC₁-C₄alkyl, formyl, C₁-C₆alkylcarbonyl, C₁-C₄alkylsulfonyl, aryl,arylsulfonyl, arylcarbonyl, heterocyclyl and heterocyclyl-substitutedC₁-C₆alkyl; each radical from the said group itself being unsubstitutedor substituted by C₁-C₄alkyl, C₁-C₄alkoxy, C₁-C₄haloalkyl, halogen,hydroxy, cyano, nitro, amino, C₁-C₄alkylamino, C₁-C₄alkyl₂amino,C₁-C₄alkylsulfonyl or arylsulfonyl; or

(3) T and U together with the group —N—C—N— form a saturated orunsaturated 5- or 6-membered heterocyclic ring which may in additioncontain as further hetero atom O or S or the hetero group—N(C₁-C₆alkyl)-;

U is hydrogen or C₁-C₆alkyl, preferably hydrogen, methyl or ethyl; and

R₂, R₂′ and R are as defined for formula (I).

Very especially preferred within the scope of formula (I), however, arecompounds of formula (X):

wherein

R₁ is —CH₂-Het;

R is C₁-C₂₀alkyl, C₂-C₂₀alkenyl or C₂-C₆alkynyl, each of those radicalsbeing unsubstituted or mono- or poly-substituted by identical ordifferent substituents, the said substituents being selected from thegroup halogen, cyano, nitro, hydroxy, C₁-C₆alkoxy, C₁-C₆alkylthio,C₁-C₆haloalkyl, C₁-C₆haloalkoxy and phenyl; or is C₃-C₇cycloalkyl thatis unsubstituted or mono- or poly-substituted by identical or differentsubstituents selected from halogen, cyano, nitro, hydroxy, C₁-C₆alkyl,C₂-C₆alkenyl, C₂-C₆alkynyl, C₁-C₆alkoxy, C₁-C₆alkylthio, C₁-C₆haloalkyl,C₁-C₂₀haloalkoxy and phenyl; or is phenyl phenoxyphenyl each of which isunsubstituted or mono- or poly-substituted by identical or differentsubstituents selected from halogen, cyano, nitro, hydroxy, C₁-C₆alkyl,C₁-C₆alkoxy, C₁-C₆alkylthio, C₁-C₆haloalkyl, C₁-C₂₀haloalkoxy;

T and U are each independently of the other hydrogen or C₁-C₆alkyl,preferably hydrogen, methyl or ethyl;

R₂ is hydrogen or C₁-C₆alkyl;

R₂′ is hydrogen or C₁-C₆alkyl; and

Het is heterocyclyl that is unsubstituted or mono- or poly-substitutedby identical or different halogen atoms.

A further especially preferred sub-group of compounds of formula (I) isformed, on account of their pronounced activity, by compounds of formula(XI):

wherein

Hal is halogen, preferably fluorine, chlorine or bromine and especiallychlorine; and especially occupies the 6-position in the pyridine;

X is CH or N and especially N;

Y is an electron-withdrawing radical, preferably cyano, nitro orC₁-C₆haloalkyl-carbonyl, especially CO—CF₃; more especially nitro;

T together with U forms a C₁-C₄alkylene bridge, preferably an ethylenebridge, which is preferably unsubstituted or substituted by methyl orethyl; and

R₂, R₂′ and R are as defined for formula (I).

Equally preferred on account of their pronounced activity is a sub-groupof compounds of formula (I) having the following formula (XII):

wherein

Hal is halogen, preferably fluorine, chlorine or bromine and especiallychlorine; and especially occupies the 2-position in the thiazole;

X is CH or N and especially N;

Y is an electron-withdrawing radical, preferably cyano, nitro orC₁-C₆haloalkyl-carbonyl, especially CO—CF₃; more especially nitro;

T together with U forms one of the groups —CH₂—CH₂—, —CH₂—CH₂—CH₂—,—CH₂—O—CH₂— and —CH₂—N(CH₃)—CH₂—, wherein all methylene groups areunsubstituted or one of said methylen groups is substituted by methyl orethyl; and

R₂, R₂′ and R are as defined in claim 1 for formula (I).

A preferred sub-group of compounds within the scope of formula (X) isformed by those compounds, wherein U is methyl or ethyl.

A further preferred group of compounds within the scope of formula (X)is formed by those compounds, wherein T is methyl or ethyl.

A further preferred sub-group of compounds within the scope of formula(X) is formed by those compounds, wherein R₂ and R₂′ are hydrogen,methyl or ethyl.

Especially preferred among the compounds within the scope of formula (X)and within the scope of preferred sub-groups mentioned above are thosecompounds in which the radical Het is pyridyl, thiazolyl ortetrahydrofuryl that is unsubstituted or mono- or di-substituted byhalogen; especially 5,6-dichloro-pyridin-3-yl, 6-chloro-pyridin-3-yl,2-chlorothiazol-5-yl and tetrahydrofuran-3-yl.

Within the scope of mentioned sub-groups, preference is given tocompounds of formula (I), wherein R is C₁-C₂₀alkyl, C₂-C₂₀alkenyl orC₂-C₆alkynyl and especially straight-chain or branched C₆-C₂₀alkyl.

Especially preferred on account of its biological activity is anycompound selected from the group of compounds 1.001; 1.008; 1.011;1.012; 1.013; 1.014; 1.015; 1.018; 1.019; 1.020; 1.021; 1.022; 1.054;1.055; 1.056; 1.057; 1.058; 1.059; 1.060; 1.061; 1.062; 1.063; 1.064;1.065; 1.066; 1.067; 1.068; 1.069; 1.070; 1.071; 1.072; 1.073; 1.074;1.075; 1.076; 1.077; 1.078; 1.079; 1.080; 1.081; 1.082; 1.083; 1.084;1.085; 1.086 and 1.087.

Parasites in the context of the present invention are parasiticarthropods and, of those, especially blood-sucking insects. Insects ofthe following orders are included: Lepidoptera, Coleoptera, Homoptera,Heteroptera, Diptera, Thysanoptera, Orthoptera, Anoplura, Siphonaptera,Mallophaga, Thysanura, Isoptera, Psocoptera and Hymenoptera. Specialmention should also be made, however, of pests that trouble human beingsor animals and transmit pathogens, e.g., flies, such as Musca domestica,Musca vetustissima, Musca autumnalis, Fannia canicularis, Sarcophagacarnaria, Lucilia sericata, Lucilia cuprina, Hypoderma bovis, Hypodermalineatum, Chrysomyia chloropyga, Dermatobia hominis, Cochliomyiahominivorax, Gasterophilus intestinalis, Oestrus ovis, Calliporaerythrocephala (=blowfly), Haematobia (=hornfly) and mosquitos, and alsoblood-sucking pests, e.g., fleas, such as Ctenocephalides felis andCtenocephalides canis (cat and dog fleas), Xenopsylla cheopis, Pulexirritans, Dermatophilus penetrans, lice, such as Damalina ovis,Pediculus humanis, stable flies and horseflies, such as Stomoxyscalcitrans, Haematopota pluvialis, Tabanus nigrovittatus, Chrysopscaecutiens, tabanids, tsetse flies, such as Glossinia species, andbiting insects, more especially cockroaches, such as Blatella germanicor Blatta orientalis and Periplaneta americana. The said parasitesattack warm-blooded animals, including farm animals, such as cows, pigs,sheep and goats; poultry, such as hens, turkeys and geese; animals bredfor their fur, such as mink, foxes, chinchillas, rabbits and the like;as well as domestic animals and pets, such as cats and dogs, and evenhuman beings do not escape attack.

Likewise, flea infestation in domestic animals and pets is a problem forthe animal owner to which as yet only unsatisfactory solutions have beenfound. Owing to the complicated life cycle of the flea, none of theknown methods of controlling fleas is totally satisfactory, especiallysince most of the known methods are aimed principally at controlling thefully grown fleas in the animal's coat and take no account at all of thevarious juvenile stages of the fleas, which live not only in theanimal's coat but also on the floor, on carpets, on the animal'ssleeping place, on chairs, in the garden and in all the other placeswith which the infested animal comes into contact. Flea treatment isgenerally expensive and must be continued for a prolonged period,success generally only being achieved when the treatment is applied notonly to the infested animal, e.g., the dog or cat, but alsosimultaneously to any places frequented by the infested animal.

The compounds of formula (I) according to the invention can be usedalone or in combination with other biocides. For example, in order toincrease the effect they can be combined with pesticides having the samedirection of action or in order to broaden the spectrum of action theycan be combined with substances having a different direction of action.It may also be of advantage to add repelling substances, so-calledrepellents. Where it is desired to extend the spectrum of action toendoparasites, e.g., worms, the compounds of formula (I) areadvantageously combined with substances having endoparasiticidalproperties. They can, of course, also be used in combination withanti-bacterial agents. Since the compounds of formula (I) are“adulticides”, that is to say since they are effective especiallyagainst the fully grown stages of the target parasites, the addition ofpesticides that are effective rather against the juvenile stages of theparasite may be very advantageous, since in that way the majority ofparasites causing large-scale economic damage will be covered.Furthermore, a substantial contribution is made to avoiding thedevelopment of resistance. Some combinations may also lead tosynergistic effects, that is to say the total amount of activeingredient applied can be reduced, which is desirable from theecological standpoint. Preferred groups of combination partners andespecially preferred combination partners are given below, it beingpossible for the combinations to comprise one or more of these partnersin addition to a compound of formula (I).

Suitable mixing partners include biocides, e.g., the insecticides andacaricides listed below, which have various mechanisms of action and arewell-known to the person skilled in the art, e.g., chitin synthesisinhibitors and growth regulators; active ingredients that act in thesame way as juvenile hormones; active ingredients that act asadulticides; broad spectrum insecticides; broad spectrum acaricides andnematicides; and also the well-known anthelmintics and substances thatrepel insects and/or acarina, the aforementioned repellents ordetachers.

Non-limiting examples of suitable insecticides and acaricides are:

(I) aldicarb; (XVIII) ethiofencarb; (XXXV) teflubenzuron; (II)azinphos-methyl; (XIX) fenitrothion; (XXXVI) terbufos; (III)benfuracarb; (XX) fenobucarb; (XXXVII) triazamate; (IV) bifenthrin;(XXI) fenvalerate; (XXXVIII) abamectin; (V) buprofezin; (XXII)formothion; (XXXIX) fenobucarb; (VI) carbofuran; (XXIII) methiocarb;(XL) tebufenozide; (VII) dibutylaminothio; (XXIV) heptenophos; (XLI)fipronil; (VIII) cartap; (XXV) imidacloprid; (XLII) beta-cyfluthrin;(IX) chlorfluazuron; (XXVI) isoprocarb; (XLIII) silafluofen; (X)chlorpyrifos; (XXVII) methamidophos; (XLIV) fenpyroximate; (XI)cyfluthrin; (XXVIII) methomyl; (XLV) pyridaben; (XII)lambda-cyhalothrin; (XXIX) mevinphos; (XLVI) fenazaquin; (XIII)alpha-cypermethrin; (XXX) parathion; (XLVII) pyriproxyfen; (XIV)zeta-cypermethrin; (XXXI) parathion-methyl; (XLVIII) pyrimidifen; (XV)deltamethrin; (XXXII) phosalone; (XLIX) nitenpyram; (XVI) diflubenzuron;(XXXIII) pirimicarb; (L) NI-25, acetamiprid; (XVII) endosulfan; (XXXIV)propoxur; (LI) avermectin B₁; (LII) an insect-active extract from aplant; (LIII) a preparation containing insect-active nematodes; (LIV) apreparation obtainable from Bacillus subtilis; (LV) a preparationcontaining insect-active fungi; (LVI) a preparation containinginsect-active viruses; (LVII) AC 303 630; (LXXXII) cis-Res-methrin;(CVIII) fenpyrad; (LVIII) acephat; (LXXXIII) clocythrin; (CIX) fenthion;(LIX) acrinathrin; (LXXXIV) clofentezin; (CX) fluazinam; (LX) alanycarb;(LXXXV) cyanophos; (CXI) flucycloxuron; (LXI) alphamethrin; (LXXXVI)cycloprothrin; (CXII) flucythrinat; (LXII) amitraz; (LXXXVII) cyhexatin;(CXIII) flufenoxuron; (LXIII) AZ 60541; (LXXXVIII) demeton M; (CXIV)flufenprox; (LXIV) azinphos A; (LXXXIX) demeton S; (CXV) fonophos; (LXV)azinphos M; (XC) demeton-S-methyl; (CXVI) fosthiazat; (LXVI)azocyclotin; (XCI) dichlofenthion; (CXVII) fubfenprox; (LXVII)bendiocarb; (XCII) dicliphos; (CXVIII) HCH; (LXVIII) bensultap; (XCIII)diethion; (CXIX) hexaflumuron; (LXIX) beta-cyfluthrin; (XCIV) dimethoat;(CXX) hexythiazox; (LXX) BPMC; (XCV) dimethylvinphos; (CXXI) iprobenfos;(LXXI) brofenprox; (XCVI) dioxathion; (CXXII) isofenphos; (LXXII)bromophos A; (XCVII) edifenphos; (CXXIII) isoxathion; (LXXIII)bufencarb; (XCVIII) emamectin; (CXXIV) ivermectin; (LXXIV)butocarboxime; (XCIX) esfenvalerat; (CXXV) lambda- (LXXV)butylpyridaben; (C) ethion; cyhalothrin; (LXXVI) cadusafos; (CI)ethofenprox; (CXXVI) malathion; (LXXVII) carbaryl; (CII) ethoprophos;(CXXVII) mecarbam; (LXXVIII) carbophenothion; (CIII) etrimphos;(CXXVIII) mesulfenphos; (CIV) fenamiphos; (CXXIX) metaldehyd; (LXXIX)chloethocarb; (CV) fenbutatinoxid; (CXXX) metolcarb; (LXXX)chlorethoxyfos; (CVI) fenothiocarb; (CXXXI) milbemectin; (LXXXI)chlormephos; (CVII) fenpropathrin; (CXXXII) moxidectin; (CXXXIII) naled;(CLXI) tefluthrin; (CLXXXVII) methoprene (CXXXIV) NC 184; (CLXII)temephos; (CLXXXVIII) hydroprene (CXXXV) omethoat; (CLXIII) terbam;(CLXXXIX) fenoxycarb (CXXXVI) oxamyl; (CLXIV) tetrachlor- (CXC)chlorfenapyr or (CXXXVII) oxydemethon M; vinphos; (CXCI) spinosad (CLXV)thiafenox; (CXXXVIII) oxydeprofos; (CLXVI) thiodicarb; (CXXXIX)permethrin; (CLXVII) thiofanox; (CXL) phenthoat; (CLXVIII) thionazin;(CXLI) phorat; (CLXIX) thuringiensin; (CXLII) phosmet; (CLXX)tralomethrin; (CXLIII) phoxim; (CLXXI) triarthen; (CXLIV) pirimiphos M;(CLXXII) triazophos; (CXLV) pirimiphos A; (CLXXIII) triazuron; (CXLVI)promecarb; (CLXXIV) trichlorfon; (CXLVII) propaphos; (CLXXV)triflumuron; (CXLVIII) prothiofos; (CLXXVI) trimethacarb; (CXLIX)prothoat; (CLXXVII) vamidothion; (CL) pyrachlophos; (CLXXVIII)xylylcarb; (CLI) pyrada-phenthion; (CLXXIX) YI 5301/5302; (CLII)pyresmethrin; (CLXXX) zetamethrin; (CLIII) pyrethrum; (CLXXXI)DPX-MP062; (CLIV) RH 5992; (CLXXXII) RH-2485; (CLV) salithion;(CLXXXIII) D 2341; (CLVI) sebufos; (CLXXXIV) XMC (CLVII) sulfotep;(3,5-xylyl (CLVIII) sulprofos; methylcarbamate), (CLIX) tebufenpyrad;(CLXXXV) lufenuron (CLX) tebupirimphos; (CLXXXVI) fluazuron

Non-limiting examples of suitable anthelmintics are mentioned below,some examples, in addition to having the anthelmintic activity, alsohaving an insecticidal and acaricidal activity and, in some cases, beingalready contained in the list above:

(A1)praziquantel=2-cyclohexylcarbonyl-4-oxo-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-α]isoquinoline

(A2)closantel=3,5-diiodo-N-[5-chloro-2-methyl-4-(a-cyano-4-chlorobenzyl)phenyl]salicylamide

(A3)triclabendazole=5-chloro-6-(2,3-dichlorophenoxy)-2-methylthio-1H-benzimidazole

(A4) levamisol=L-(−)-2,3,5,6-tetrahydro-6-phenylimidazo[2,1b]thiazole

(A5) mebendazole=(5-benzoyl-1H-benzimidazol-2-yl)carbamic acid methylester

(A6) omphalotin=a macrocyclic fermentation product of the fungusOmphalotus olearius described in WO 97/20857

(A7) abamectin=avermectin B1

(A8) ivermectin=22,23-dihydroavermectin B1

(A9)moxidectin=5-O-demethyl-28-deoxy-25-(1,3-dimethyl-1-butenyl)-6,28-epoxy-23-(methoxyimino)-milbemycinB

(A10)doramectin=25-cyclohexyl-5-O-demethyl-25-de(1-methylpropyl)-avermectinA1a

(A11) milbemectin=mixture of milbemycin A3 and milbemycin A4

(A12) milbemycinoxim=5-oxime of milbemectin

Non-limiting examples of suitable repelling substances (repellents ordetachers) are:

(R1) DEET (N,N-diethyl-m-toluamide)

(R2) KBR 3023 N-butyl-2-oxycarbonyl-(2-hydroxy)-piperidine

(R3) cymiazole=N-2,3-dihydro-3-methyl-1,3-thiazol-2-ylidene-2,4-xylidene

The said mixing partners are well-known to experts in the field. Most ofthem are described in the various editions of the Pesticide Manual, TheBritish Crop Protection Council, London, and others are described in thevarious editions of The Merck Index, Merck & Co., Inc., Rahway, N.J.,USA or in the patent literature. The following list therefore confinesitself to giving some examples of sources.

(I) 2-methyl-2-(methylthio)propionaldehyde-O-methylcarbamoyloxime(aldicarb), from The Pesticide Manual, 11^(th) ed. (1997), The BritishCrop Protection Council, London, page 26;

(II)S-(3,4-dihydro-4-oxobenzo[d]-[1,2,3]-triazin-3-ylmethyl)O,O-dimethyl-phosphorodithioate(azinphos-methyl), from The Pesticide Manual, 11^(th) ed. (1997), TheBritish Crop Protection Council, London, page 67;

(III)ethyl-N-[2,3-dihydro-2,2-dimethylbenzofuran-7-yloxycarbonyl-(methyl)aminothio]-N-isopropyl-β-alaninate(benfuracarb), from The Pesticide Manual, 11^(th) ed. (1997), TheBritish Crop Protection Council, London, page 96;

(IV)2-methylbiphenyl-3-ylmethyl-(Z)-(1RS)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate(bifenthrin), from The Pesticide Manual, 11^(th) ed. (1997), The BritishCrop Protection Council, London, page 118;

(V) 2-tert-butylimino-3-isopropyl-5-phenyl-1,3,5-thiadiazian-4-one(buprofezin), from The Pesticide Manual, 11^(th) ed. (1997), The BritishCrop Protection Council, London, page 157;

(VI) 2,3-dihydro-2,2-dimethylbenzofuran-7-yl-methylcarbamate(carbofuran), from The Pesticide Manual, 11^(th) ed. (1997), The BritishCrop Protection Council, London, page 186;

(VII)2,3-dihydro-2,2-dimethylbenzofuran-7-yl-(dibutylaminothio)methylcarbamate(carbosulfan), from The Pesticide Manual, 11^(th) ed. (1997), TheBritish Crop Protection Council, London, page 188;

(VIII) S,S′-(2-dimethylaminotrimethylene)-bis(thiocarbamate) (cartap),from The Pesticide Manual, 11^(th) ed. (1997), The British CropProtection Council, London, page 193;

(IX)1-[3,5-dichloro-4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenyl]-3-(2,6-difluorobenzoyl)-urea(chlorfluazuron), from The Pesticide Manual, 11^(th) ed. (1997), TheBritish Crop Protection Council, London, page 213;

(X) O,O-diethyl-O-3,5,6-trichloro-2-pyridyl-phosphorothioate(chlorpyrifos), from The Pesticide Manual, 11^(th) ed. (1997), TheBritish Crop Protection Council, London, page 235;

(XI) (RS)-α-cyano-4-fluoro-3-phenoxybenzyl-(1RS,3RS; 1RS,3RS)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate(cyfluthrin), from The Pesticide Manual, 11^(th) ed. (1997), The BritishCrop Protection Council, London, page 293;

(XII) mixture of(S)-α-cyano-3-phenoxybenzyl-(Z)-(1R,3R)-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylateand(R)-α-cyano-3-phenoxybenzyl-(Z)-(1R,3R)-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate(lambda-cyhalothrin), from The Pesticide Manual, 11^(th) ed. (1997), TheBritish Crop Protection Council, London, page 300;

(XIII) racemate consisting of(S)-α-cyano-3-phenoxybenzyl-(1R,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylateand(R)-α-cyano-3-phenoxybenzyl-(1S,3S)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate(alpha-cypermethrin), from The Pesticide Manual, 11^(th) ed. (1997), TheBritish Crop Protection Council, London, page 308;

(XIV) a mixture of the stereoisomers of (S)-α-cyano-3-phenoxybenzyl(1RS,3RS,1RS,3RS)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate(zeta-cypermethrin), from The Pesticide Manual, 11^(th) ed. (1997), TheBritish Crop Protection Council, London, page 314;

(XV)(S)-α-cyano-3-phenoxybenzyl-(1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate(deltamethrin), from The Pesticide Manual, 11^(th) ed. (1997), TheBritish Crop Protection Council, London, page 344;

(XVI) (4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea (diflubenzuron), fromThe Pesticide Manual, 11^(th) ed. (1997), The British Crop ProtectionCouncil, London, page 395;

(XVII)(1,4,5,6,7,7-hexachloro-8,9,10-trinorborn-5-en-2,3-ylenebismethylene)-sulfite(endosulfan), from The Pesticide Manual, 11^(th) ed. (1997), The BritishCrop Protection Council, London, page 459;

(XVIII) α-ethylthio-o-tolyl-methylcarbamate (ethiofencarb), from ThePesticide Manual, 11^(th) ed. (1997), The British Crop ProtectionCouncil, London, page 479;

(XIX) O,O-dimethyl-O-4-nitro-m-tolyl-phosphorothioate (fenitrothion),from The Pesticide Manual, 11^(th) ed. (1997), The British CropProtection Council, London, page 514;

(XX) 2-sec-butylphenyl-methylcarbamate (fenobucarb), from The PesticideManual, 11^(th) ed. (1997), The British Crop Protection Council, London,page 516;

(XXI)(RS)-α-cyano-3-phenoxybenzyl-(RS)-2-(4-chlorophenyl)-3-methylbutyrate(fenvalerate), from The Pesticide Manual, 11^(th) ed. (1997), TheBritish Crop Protection Council, London, page 539;

(XXII) S-[formyl(methyl)carbamoylmethyl]-O,O-dimethyl-phosphorodithioate(formothion), from The Pesticide Manual, 11^(th) ed. (1997), The BritishCrop Protection Council, London, page 625;

(XXIII) 4-methylthio-3,5-xylyl-methylcarbamate (methiocarb), from ThePesticide Manual, 11^(th) ed. (1997), The British Crop ProtectionCouncil, London, page 813;

(XXIV) 7-chlorobicyclo[3.2.0]hepta-2,6-dien-6-yl-dimethylphosphate(heptenophos), from The Pesticide Manual, 11^(th) ed. (1997), TheBritish Crop Protection Council, London, page 670;

(XXV) 1-(6-chloro-3-pyridylmethyl)-N-nitroimidazolidin-2-ylideneamine(imidacloprid), from The Pesticide Manual, 11^(th) ed. (1997), TheBritish Crop Protection Council, London, page 706;

(XXVI) 2-isopropylphenyl-methylcarbamate (isoprocarb), from ThePesticide Manual, 11^(th) ed. (1997), The British Crop ProtectionCouncil, London, page 729;

(XXVI) O,S-dimethyl-phosphoramidothioate (methamidophos), from ThePesticide Manual, 11^(th) ed. (1997), The British Crop ProtectionCouncil, London, page 808;

(XXVIII) S-methyl-N-(methylcarbamoyloxy)thioacetimidate (methomyl), fromThe Pesticide Manual, 11^(th) ed. (1997), The British Crop ProtectionCouncil, London, page 815;

(XXIX) methyl-3-(dimethoxyphosphinoyloxy)but-2-enoate (mevinphos), fromThe Pesticide Manual, 11^(th) ed. (1997), The British Crop ProtectionCouncil, London, page 844;

(XXX) O,O-diethyl-O-4-nitrophenyl-phosphorothioate (parathion), from ThePesticide Manual, 11^(th) ed. (1997), The British Crop ProtectionCouncil, London, page 926;

(XXXI) O,O-dimethyl-O-4-nitrophenyl-phosphorothioate (parathion-methyl),from The Pesticide Manual, 11^(th) ed. (1997), The British CropProtection Council, London, page 928;

(XXXII)S-6-chloro-2,3-dihydro-2-oxo-1,3-benzoxazol-3-ylmethyl-O,O-diethyl-phosphoro-dithioate(phosalone), from The Pesticide Manual, 11^(th) ed. (1997), The BritishCrop Protection Council, London, page 963;

(XXXIII) 2-dimethylamino-5,6-dimethylpyrimidin-4-yl-dimethylcarbamate(pirimicarb), from The Pesticide Manual, 11^(th) ed. (1997), The BritishCrop Protection Council, London, page 985;

(XXXIV) 2-isopropoxyphenyl-methylcarbamate (propoxur), from ThePesticide Manual, 11^(th) ed. (1997), The British Crop ProtectionCouncil, London, page 1036;

(XXXV) 1-(3,5-dichloro-2,4-difluorophenyl)-3-(2,6-difluorobenzoyl)urea(teflubenzuron), from The Pesticide Manual, 11^(th) ed. (1997), TheBritish Crop Protection Council, London, page 1158;

(XXXVI) S-tert-butylthiomethyl-O,O-dimethyl-phosphorodithioate(terbufos), from The Pesticide Manual, 11^(th) ed. (1997), The BritishCrop Protection Council, London, page 1165;

(XXXVII)ethyl-(3-tert-butyl-1-dimethylcarbamoyl-1H-1,2,4-triazol-5-yl-thio)-acetate,(triazamate), from The Pesticide Manual, 11^(th) ed. (1997), The BritishCrop Protection Council, London, page 1224;

(XXXVIII) abamectin, from The Pesticide Manual, 11^(th) ed. (1997), TheBritish Crop Protection Council, London, page 3;

(XXXIX) 2-sec-butylphenyl-methylcarbamate (fenobucarb), from ThePesticide Manual, 11^(th) ed. (1997), The British Crop ProtectionCouncil, London, page 516;

(XL) N-tert-butyl-N′-(4-ethylbenzoyl)-3,5-dimethylbenzohydrazide(tebufenozide), from The Pesticide Manual, 11^(th) ed. (1997), TheBritish Crop Protection Council, London, page 1147;

(XLI)(±)-5-amino-1-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)-4-trifluoromethyl-sulfinylpyrazole-3-carbonitrile(fipronil), from The Pesticide Manual, 11^(th) ed. (1997), The BritishCrop Protection Council, London, page 545;

(XLII)(RS)-α-cyano-4-fluoro-3-phenoxybenzyl(1RS,3RS;1RS,3RS)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate(beta-cyfluthrin), from The Pesticide Manual, 11^(th) ed. (1997), TheBritish Crop Protection Council, London, page 295;

(XLIII)(4-ethoxyphenyl)-[3-(4-fluoro-3-phenoxyphenyl)propyl](dimethyl)silane(silafluofen), from The Pesticide Manual, 11^(th) ed. (1997), TheBritish Crop Protection Council, London, page 1105;

(XLIV) tert-butyl(E)-α-(1,3-dimethyl-5-phenoxypyrazol-4-yl-methyleneamino-oxy)-p-toluate(fenpyroximate), from The Pesticide Manual, 11^(th) ed. (1997), TheBritish Crop Protection Council, London, page 530;

(XLV)2-tert-butyl-5-(4-tert-butylbenzylthio)-4-chloropyridazin-3(2H)-one(pyridaben), from The Pesticide Manual, 11^(th) ed. (1997), The BritishCrop Protection Council, London, page 1161;

(XLVI) 4-[[4-(1,1-dimethylphenyl)phenyl]ethoxy]-quinazoline(fenazaquin), from The Pesticide Manual, 11^(th) ed. (1997), The BritishCrop Protection Council, London, page 507;

(XLVII) 4-phenoxyphenyl-(RS)-2-(pyridyloxy)propyl ether (pyriproxyfen),from The Pesticide Manual, 11^(th) ed. (1997), The British CropProtection Council, London, page 1073;

(XLVIII)5-chloro-N-{2-[4-(2-ethoxyethyl)-2,3-dimethylphenoxy]ethyl}-6-ethylpyrimidine-4-amine(pyrimidifen), from The Pesticide Manual, 11^(th) ed. (1997), TheBritish Crop Protection Council, London, page 1070;

(XLIX)(E)-N-(6-chloro-3-pyridylmethyl)-N-ethyl-N′-methyl-2-nitrovinylidenediamine(nitenpyram), from The Pesticide Manual, 11^(th) ed. (1997), The BritishCrop Protection Council, London, page 880;

(L) (E)-N¹-[(6-chloro-3-pyridyl)methyl]-N²-cyano-N¹-methylacetamidine(NI-25, acetamiprid), from The Pesticide Manual, 11^(th) ed. (1997), TheBritish Crop Protection Council, London, page 9;

(LI) avermectin B₁, from The Pesticide Manual, 11^(th) ed. (1997), TheBritish Crop Protection Council, London, page 3;

(LII) an insect-active extract from a plant, especially(2R,6aS,12aS)-1,2,6,6a,12,12a-hexahydro-2-isopropenyl-8,9-dimethoxy-chromeno[3,4-b]furo[2,3-h]chromen-6-one(rotenone), from The Pesticide Manual, 11^(th) ed. (1997), The BritishCrop Protection Council, London, page 1097; and an extract fromAzadirachta indica, especially azadirachtin, from The Pesticide Manual,11^(th) ed. (1997), The British Crop Protection Council, London, page59; and

(LIII) a preparation containing insect-active nematodes, preferablyHeterorhabditis bacteriophora and Heterorhabditis megidis, from ThePesticide Manual, 11^(th) ed. (1997), The British Crop ProtectionCouncil, London, page 671; Steinernema feltiae, from The PesticideManual, 11^(th) ed. (1997), The British Crop Protection Council, London,page 1115, and Steinernema scapterisci, from The Pesticide Manual,11^(th) ed. (1997), The British Crop Protection Council, London, page1116;

(LIV) a preparation, obtainable from Bacillus subtilis, from ThePesticide Manual, 11^(th) ed. (1997), The British Crop ProtectionCouncil, London, page 72; or from a Bacillus thuringiensis strain withthe exception of compounds isolated from GC91 or from NCTC11821; ThePesticide Manual, 11^(th) ed. (1997), The British Crop ProtectionCouncil, London, page 73;

(LV) a preparation containing insect-active fungi, preferablyVerticillium lecanii, from The Pesticide Manual, 11^(th) ed. (1997), TheBritish Crop Protection Council, London, page 1266; Beauveriabrogniartii, from The Pesticide Manual, 11^(th) ed. (1997), The BritishCrop Protection Council, London, page 85; and Beauveria bassiana, fromThe Pesticide Manual, 11^(th) ed. (1997), The British Crop ProtectionCouncil, London, page 83;

(LVI) a preparation containing insect-active viruses, preferablyNeodipridon Sertifer NPV, from The Pesticide Manual, 11^(th) ed. (1997),The British Crop Protection Council, London, page 1342; Mamestrabrassicae NPV, from The Pesticide Manual, 11^(th) ed. (1997), TheBritish Crop Protection Council, London, page 759; and Cydia pomonellagranulosis virus, from The Pesticide Manual, 11^(th) ed. (1997), TheBritish Crop Protection Council, London, page 291;

(CLXXXI)7-chloro-2,3,4a,5-tetrahydro-2-[methoxycarbonyl(4-trifluoromethoxyphenyl)carbamoyl]indol[1,2e]oxazoline-4a-carboxylate(DPX-MP062, indoxycarb), from The Pesticide Manual, 11^(th) ed. (1997),The British Crop Protection Council, London, page 453;

(CLXXXII)N′-tert-butyl-N′-(3,5-dimethylbenzoyl)-3-methoxy-2-methylbenzohydrazide(RH-2485, methoxyfenozide), from The Pesticide Manual, 11^(th) ed.(1997), The British Crop Protection Council, London, page 1094; and

(CLXXXIII) (N′-[4-methoxy-biphenyl-3-yl]-hydrazinecarboxylic acidisopropyl ester (D 2341), from Brighton Crop Protection Conference, pp.487-493 (1996);

(R2) Book of Abstracts, 212th ACS National Meeting Orlando, Fla., Aug.25-29, 1996, AGRO-020. Publisher: American Chemical Society, Washington,D.C. CONEN: 63BFAF.

In accordance with the above remarks, a further important aspect of thepresent invention relates to combination preparations for controllingparasites on warm-blooded animals which comprise, in addition to acompound of formula (I), at least one further active ingredient havingthe same or a different direction of action and at least onephysiologically tolerable carrier. The present invention is notrestricted to two-component combinations.

Within the scope of the present invention preference is given, forexample, to the following two-component combinations, the figure inparenthesis representing one of the combination partners mentioned aboveand the number following the symbol “&” representing a compound from theTables which follow:

(IX) & 1.001; (IX) & 1.008; (IX) & 1.011; (IX) & 1.012; (IX) & 1.013;(IX) & 1.014; (IX) & 1.015; (IX) & 1.018; (IX) & 1.019; (IX) & 1.020;(IX) & 1.021; (IX) & 1.022; (IX) & 1.054; (IX) & 1.055; (IX) & 1.056;(IX) & 1.057; (IX) & 1.058; (XIII) & 1.001; (XIII) & 1.008; (XIII) &1.011; (XIII) & 1.012; (XIII) & 1.013; (XIII) & 1.014; (XIII) & 1.015;(XIII) & 1.018; (XIII) & 1.019; (XIII) & 1.020; (XIII) & 1.021; (XIII) &1.022; (XIII) & 1.054; (XIII) & 1.055; (XIII) & 1.056; (XIII) & 1.057;(XIII) & 1.058; (XIV) & 1.001; (XIV) & 1.008; (XIV) & 1.011; (XIV) &1.012; (XIV) & 1.013; (XIV) & 1.014; (XIV) & 1.015; (XIV) & 1.018; (XIV)& 1.019; (XIV) & 1.020; (XIV) & 1.021; (XIV) & 1.022; (XIV) & 1.054;(XIV) & 1.055; (XIV) & 1.056; (XIV) & 1.057; (XIV) & 1.058; (LI) &1.001; (LI) & 1.008; (LI) & 1.011; (LI) & 1.012; (LI) & 1.013; (LI) &1.014; (LI) & 1.015; (LI) & 1.018; (LI) & 1.019; (LI) & 1.020; (LI) &1.021; (LI) & 1.022; (LI) & 1.054; (LI) & 1.055; (LI) & 1.056; (LI) &1.057; (LI) & 1.058; (XXV) & 1.001; (XXV) & 1.008; (XXV) & 1.011; (XXV)& 1.012; (XXV) & 1.013; (XXV) & 1.014; (XXV) & 1.015; (XXV) & 1.018;(XXV) & 1.019; (XXV) & 1.020; (XXV) & 1.021; (XXV) & 1.022; (XXV) &1.054; (XXV) & 1.055; (XXV) & 1.056; (XXV) & 1.057; (XXV) & 1.058;(XXXV) & 1.001; (XXXV) & 1.008; (XXXV) & 1.011; (XXXV) & 1.012; (XXXV) &1.013; (XXXV) & 1.014; (XXXV) & 1.015; (XXXV) & 1.018; (XXXV) & 1.019;(XXXV) & 1.020; (XXXV) & 1.021; (XXXV) & 1.022; (XXXV) & 1.054; (XXXV) &1.055; (XXXV) & 1.056; (XXXV) & 1.057; (XXXV) & 1.058; (XXXVIII) &1.001; (XXXVIII) & 1.008; (XXXVIII) & 1.011; (XXXVIII) & 1.012;(XXXVIII) & 1.013; (XXXVIII) & 1.014; (XXXVIII) & 1.015; (XXXVIII) &1.018; (XXXVIII) & 1.019; (XXXVIII) & 1.020; (XXXVIII) & 1.021;(XXXVIII) & 1.022; (XXXVIII) & 1.054; (XXXVIII) & 1.055; (XXXVIII) &1.056; (XXXVIII) & 1.057; (XXXVIII) & 1.058; (XLI) & 1.001; (XLI) &1.008; (XLI) & 1.011; (XLI) & 1.012; (XLI) & 1.013; (XLI) & 1.014; (XLI)& 1.015; (XLI) & 1.018; (XLI) & 1.019; (XLI) & 1.020; (XLI) & 1.021;(XLI) & 1.022; (XLI) & 1.054; (XLI) & 1.055; (XLI) & 1.056; (XLI) &1.057; (XLI) & 1.058; (XLVII) & 1.001; (XLVII) & 1.008; (XLVII) & 1.011;(XLVII) & 1.012; (XLVII) & 1.013; (XLVII) & 1.014; (XLVII.) & 1.015;(XLVII) & 1.018; (XLVII) & 1.019; (XLVII) & 1.020; (XLVII) & 1.021;(XLVII) & 1.022; (XLVII) & 1.054; (XLVII) & 1.055; (XLVII) & 1.056;(XLVII) & 1.057; (XLVII) & 1.058; (XLIX) & 1.001; (XLIX) & 1.008; (XLIX)& 1.011; (XLIX) & 1.012; (XLIX) & 1.013; (XLIX) & 1.014; (XLIX) & 1.015;(XLIX) & 1.018; (XLIX) & 1.019; (XLIX) & 1.020; (XLIX) & 1.021; (XLIX) &1.022; (XLIX) & 1.054; (XLIX) & 1.055; (XLIX) & 1.056; (XLIX) & 1.057;(XLIX) & 1.058; (LXI) & 1.001; (LXI) & 1.008; (LXI) & 1.011; (LXI) &1.012; (LXI) & 1.013; (LXI) & 1.014; (LXI) & 1.015; (LXI) & 1.018; (LXI)& 1.019; (LXI) & 1.020; (LXI) & 1.021; (LXI) & 1.022; (LXI) & 1.054;(LXI) & 1.055; (LXI) & 1.056; (LXI) & 1.057; (LXI) & 1.058; (LXII) &1.001; (LXII) & 1.008; (LXII) & 1.011; (LXII) & 1.012; (LXII) & 1.013;(LXII) & 1.014; (LXII) & 1.015; (LXII) & 1.018; (LXII) & 1.019; (LXII) &1.020; (LXII) & 1.021; (LXII) & 1.022; (LXII) & 1.054; (LXII) & 1.055;(LXII) & 1.056; (LXII) & 1.057; (LXII) & 1.058; (CIX) & 1.001; (CIX) &1.008; (CIX) & 1.011; (CIX) & 1.012; (CIX) & 1.013; (CIX) & 1.014; (CIX)& 1.015; (CIX) & 1.018; (CIX) & 1.019; (CIX) & 1.020; (CIX) & 1.021;(CIX) & 1.022; (CIX) & 1.054; (CIX) & 1.055; (CIX) & 1.056; (CIX) &1.057; (CIX) & 1.058; (CXIII) & 1.001; (CXIII) & 1.008; (CXIII) & 1.011;(CXIII) & 1.012; (CXIII) & 1.013; (CXIII) & 1.014; (CXIII) & 1.015;(CXIII) & 1.018; (CXIII) & 1.019; (CXIII) & 1.020; (CXIII) & 1.021;(CXIII) & 1.022; (CXIII) & 1.054; (CXIII) & 1.055; (CXIII) & 1.056;(CXIII) & 1.057; (CXIII) & 1.058; (CXIX) & 1.001; (CXIX) & 1.008; (CXIX)& 1.011; (CXIX) & 1.012; (CXIX) & 1.013; (CXIX) & 1.014; (CXIX) & 1.015;(CXIX) & 1.018; (CXIX) & 1.019; (CXIX) & 1.020; (CXIX) & 1.021; (CXIX) &1.022; (CXIX) & 1.054; (CXIX) & 1.055; (CXIX) & 1.056; (CXIX) & 1.057;(CXIX) & 1.058; (CXXIV) & 1.001; (CXXIV) & 1.008; (CXXIV) & 1.011;(CXXIV) & 1.012; (CXXIV) & 1.013; (CXXIV) & 1.014; (CXXIV) & 1.015;(CXXIV) & 1.018; (CXXIV) & 1.019; (CXXIV) & 1.020; (CXXIV) & 1.021;(CXXIV) & 1.022; (CXXIV) & 1.054; (CXXIV) & 1.055; (CXXIV) & 1.056;(CXXIV) & 1.057; (CXXIV) & 1.058; (CXXXI) & 1.001; (CXXXI) & 1.008;(CXXXI) & 1.011; (CXXXI) & 1.012; (CXXXI) & 1.013; (CXXXI) & 1.014;(CXXXI) & 1.015; (CXXXI) & 1.018; (CXXXI) & 1.019; (CXXXI) & 1.020;(CXXXI) & 1.021; (CXXXI) & 1.022; (CXXXI) & 1.054; (CXXXI) & 1.055;(CXXXI) & 1.056; (CXXXI) & 1.057; (CXXXI) & 1.058; (CXXXII) & 1.001;(CXXXII) & 1.008; (CXXXII) & 1.011; (CXXXII) & 1.012; (CXXXII) & 1.013;(CXXXII) & 1.014; (CXXXII) & 1.015; (CXXXII) & 1.018; (CXXXII) & 1.019;(CXXXII) & 1.020; (CXXXII) & 1.021; (CXXXII) & 1.022; (CXXXII) & 1.054;(CXXXII) & 1.055; (CXXXII) & 1.056; (CXXXII) & 1.057; (CXXXII) & 1.058;(CXXXIX) & 1.001; (CXXXIX) & 1.008; (CXXXIX) & 1.011; (CXXXIX) & 1.012;(CXXXIX) & 1.013; (CXXXIX) & 1.014; (CXXXIX) & 1.015; (CXXXIX) & 1.018;(CXXXIX) & 1.019; (CXXXIX) & 1.020; (CXXXIX) & 1.021; (CXXXIX) & 1.022;(CXXXIX) & 1.054; (CXXXIX) & 1.055; (CXXXIX) & 1.056; (CXXXIX) & 1.057;(CXXXIX) & 1.058; (CLII) & 1.001; (CLII) & 1.008; (CLII) & 1.011; (CLII)& 1.012; (CLII) & 1.013; (CLII) & 1.014; (CLII) & 1.015; (CLII) & 1.018;(CLII) & 1.019; (CLII) & 1.020; (CLII) & 1.021; (CLII) & 1.022; (CLII) &1.054; (CLII) & 1.055; (CLII) & 1.056; (CLII) & 1.057; (CLII) & 1.058;(CLIII) & 1.001; (CLIII) & 1.008; (CLIII) & 1.011; (CLIII) & 1.012;(CLIII) & 1.013; (CLIII) & 1.014; (CLIII) & 1.015; (CLIII) & 1.018;(CLIII) & 1.019; (CLIII) & 1.020; (CLIII) & 1.021; (CLIII) & 1.022;(CLIII) & 1.054; (CLIII) & 1.055; (CLIII) & 1.056; (CLIII) & 1.057;(CLIII) & 1.058; (CLIX) & 1.001; (CLIX) & 1.008; (CLIX) & 1.011; (CLIX)& 1.012; (CLIX) & 1.013; (CLIX) & 1.014; (CLIX) & 1.015; (CLIX) & 1.018;(CLIX) & 1.019; (CLIX) & 1.020; (CLIX) & 1.021; (CLIX) & 1.022; (CLIX) &1.054; (CLIX) & 1.055; (CLIX) & 1.056; (CLIX) & 1.057; (CLIX) & 1.058;(CLXXIII) & 1.001; (CLXXIII) & 1.008; (CLXXIII) & 1.011; (CLXXIII) &1.012; (CLXXIII) & 1.013; (CLXXIII) & 1.014; (CLXXIII) & 1.015;(CLXXIII) & 1.018; (CLXXIII) & 1.019; (CLXXIII) & 1.020; (CLXXIII) &1.021; (CLXXIII) & 1.022; (CLXXIII) & 1.054; (CLXXIII) & 1.055;(CLXXIII) & 1.056; (CLXXIII) & 1.057; (CLXXIII) & 1.058; (CLXXV) &1.001; (CLXXV) & 1.008; (CLXXV) & 1.011; (CLXXV) & 1.012; (CLXXV) &1.013; (CLXXV) & 1.014; (CLXXV) & 1.015; (CLXXV) & 1.018; (CLXXV) &1.019; (CLXXV) & 1.020; (CLXXV) & 1.021; (CLXXV) & 1.022; (CLXXV) &1.054; (CLXXV) & 1.055; (CLXXV) & 1.056; (CLXXV) & 1.057; (CLXXV) &1.058; (CLXXXI) & 1.001; (CLXXXI) & 1.008; (CLXXXI) & 1.011; (CLXXXI) &1.012; (CLXXXI) & 1.013; (CLXXXI) & 1.014; (CLXXXI) & 1.015; (CLXXXI) &1.018; (CLXXXI) & 1.019; (CLXXXI) & 1.020; (CLXXXI) & 1.021; (CLXXXI) &1.022; (CLXXXI) & 1.054; (CLXXXI) & 1.055; (CLXXXI) & 1.056; (CLXXXI) &1.057; (CLXXXI) & 1.058; (CLXXXV) & 1.001; (CLXXXV) & 1.008; (CLXXXV) &1.011; (CLXXXV) & 1.012; (CLXXXV) & 1.013; (CLXXXV) & 1.014; (CLXXXV) &1.015; (CLXXXV) & 1.018; (CLXXXV) & 1.019; (CLXXXV) & 1.020; (CLXXXV) &1.021; (CLXXXV) & 1.022; (CLXXXV) & 1.054; (CLXXXV) & 1.055; (CLXXXV) &1.056; (CLXXXV) & 1.057; (CLXXXV) & 1.058; (CLXXXVI) & 1.001; (CLXXXVI)& 1.008; (CLXXXVI) & 1.011; (CLXXXVI) & 1.012; (CLXXXVI) & 1.013;(CLXXXVI) & 1.014; (CLXXXVI) & 1.015; (CLXXXVI) & 1.018; (CLXXXVI) &1.019; (CLXXXVI) & 1.020; (CLXXXVI) & 1.021; (CLXXXVI) & 1.022;(CLXXXVI) & 1.054; (CLXXXVI) & 1.055; (CLXXXVI) & 1.056; (CLXXXVI) &1.057; (CLXXXVI) & 1.058; (CLXXXVII) & 1.001; (CLXXXVII) & 1.008;(CLXXXVII) & 1.011; (CLXXXVII) & 1.012; (CLXXXVII) & 1.013; (CLXXXVII) &1.014; (CLXXXVII) & 1.015; (CLXXXVII) & 1.018; (CLXXXVII) & 1.019;(CLXXXVII) & 1.020; (CLXXXVII) & 1.021; (CLXXXVII) & 1.022; (CLXXXVII) &1.054; (CLXXXVII) & 1.055; (CLXXXVII) & 1.056; (CLXXXVII) & 1.057;(CLXXXVII) & 1.058; (CLXXXVIII) & 1.001; (CLXXXVIII) & 1.008;(CLXXXVIII) & 1.011; (CLXXXVIII) & 1.012; (CLXXXVIII) & 1.013;(CLXXXVIII) & 1.014; (CLXXXVIII) & 1.015; (CLXXXVIII) & 1.018;(CLXXXVIII) & 1.019; (CLXXXVIII) & 1.020; (CLXXXVIII) & 1.021;(CLXXXVIII) & 1.022; (CLXXXVIII) & 1.054; (CLXXXVIII) & 1.055;(CLXXXVIII) & 1.056; (CLXXXVIII) & 1.057; (CLXXXVIII) & 1.058; (CLXXXIX)& 1.001; (CLXXXIX) & 1.008; (CLXXXIX) & 1.011; (CLXXXIX) & 1.012;(CLXXXIX) & 1.013; (CLXXXIX) & 1.014; (CLXXXIX) & 1.015; (CLXXXIX) &1.018; (CLXXXIX) & 1.019; (CLXXXIX) & 1.020; (CLXXXIX) & 1.021;(CLXXXIX) & 1.022; (CLXXXIX) & 1.054; (CLXXXIX) & 1.055; (CLXXXIX) &1.056; (CLXXXIX) & 1.057; (CLXXXIX) & 1.058; (CXC) & 1.001; (CXC) &1.008; (CXC) & 1.011; (CXC) & 1.012; (CXC) & 1.013; (CXC) & 1.014; (CXC)& 1.015; (CXC) & 1.018; (CXC) & 1.019; (CXC) & 1.020; (CXC) &1.021;(CXC) & 1.022;(CXC) & 1.054; (CXC) & 1.055; (CXC) & 1.056; (CXC) &1.057; (CXC) & 1.058; (CXCL) & 1.001; (CXCL) & 1.008; (CXCL) & 1.011;(CXCL) & 1.012; (CXCL) & 1.013; (CXCL) & 1.014; (CXCL) & 1.015; (CXCL) &1.018; (CXCL) & 1.019; (CXCL) & 1.020; (CXCL) & 1.021; (CXCL) & 1.022;(CXCL) & 1.054; (CXCL) & 1.055; (CXCL) & 1.056; (CXCL) & 1.057; (CXCL) &1.058; (A1) & 1.001; (A1) & 1.008; (A1) & 1.011; (A1) & 1.012; (A1) &1.013; (A1) & 1.014; (A1) & 1.015; (A1) & 1.018; (A1) & 1.019; (A1) &1.020; (A1) & 1.021; (A1) & 1.022; (A1) & 1.054; (A1) & 1.055; (A1) &1.056; (A1) & 1.057; (A1) & 1.058; (A2) & 1.001; (A2) & 1.008; (A2) &1.011; (A2) & 1.012; (A2) & 1.013; (A2) & 1.014; (A2) & 1.015; (A2) &1.018; (A2) & 1.019; (A2) & 1.020; (A2) & 1.021; (A2) & 1.022; (A2) &1.054; (A2) & 1.055; (A2) & 1.056; (A2) & 1.057; (A2) & 1.058; (A3) &1.001; (A3) & 1.008; (A3) & 1.011; (A3) & 1.012; (A3) & 1.013; (A3) &1.014; (A3) & 1.015; (A3) & 1.018; (A3) & 1.019; (A3) & 1.020; (A3) &1.021; (A3) & 1.022; (A3) & 1.054; (A3) & 1.055; (A3) & 1.056; (A3) &1.057; (A3) & 1.058; (A4) & 1.001; (A4) & 1.008; (A4) & 1.011; (A4) &1.012; (A4) & 1.013; (A4) & 1.014; (A4) & 1.015; (A4) & 1.018; (A4) &1.019; (A4) & 1.020; (A4) & 1.021; (A4) & 1.022; (A4) & 1.054; (A4) &1.055; (A4) & 1.056; (A4) & 1.057; (A4) & 1.058; (A5) & 1.001; (A5) &1.008; (A5) & 1.011; (A5) & 1.012; (A5) & 1.013; (A5) & 1.014; (A5) &1.015; (A5) & 1.018; (A5) & 1.019; (A5) & 1.020; (A5) & 1.021; (A5) &1.022; (A5) & 1.054; (A5) & 1.055; (A5) & 1.056; (A5) & 1.057; (A5) &1.058; (A6) & 1.001; (A6) & 1.008; (A6) & 1.011; (A6) & 1.012; (A6) &1.014; (A6) & 1.015; (A6) & 1.018; (A6) & 1.019; (A6) & 1.020; (A6) &1.021; (A6) & 1.022; (A6) & 1.054; (A6) & 1.055; (A6) & 1.056; (A6) &1.057; (A6) & 1.058; (A10) & 1.001; (A10) & 1.008; (A10) & 1.011; (A10)& 1.012; (A10) & 1.013; (A10) & 1.014; (A10) & 1.015; (A10) & 1.018;(A10) & 1.019; (A10) & 1.020; (A10) & 1.021; (A10) & 1.022; (A10) &1.054; (A10) & 1.055; (A10) & 1.056; (A10) & 1.057; (A10) & 1.058; (A11)& 1.001; (A11) & 1.018; (A11) & 1.011; (A11) & 1.012; (A11) & 1.013;(A11) & 1.014; (A11) & 1.015; (A11) & 1.018; (A11) & 1.019; (A11) &1.020; (A11) & 1.021; (A11) & 1.022; (A11) & 1.054; (A11) & 1.055; (A11)& 1.056; (A11) & 1.057; (A11) & 1.058; (R1) & 1.001; (R1) & 1.008; (R1)& 1.011; (R1) & 1.012; (R1) & 1.013; (R1) & 1.014; (R1) & 1.015; (R1) &1.018; (R1) & 1.019; (R1) & 1.020; (R1) & 1.021; (R1) & 1.022; (R1) &1.054; (R1) & 1.055; (R1) & 1.056; (R1) & 1.057; (R1) & 1.058; (R2) &1.001; (R2) & 1.008; (R2) & 1.011; (R2) & 1.012; (R2) & 1.013; (R2) &1.014; (R2) & 1.015; (R2) & 1.018; (R2) & 1.019; (R2) & 1.020; (R2) &1.021; (R2) & 1.022; (R2) & 1.054; (R2) & 1.055; (R2) & 1.056; (R2) &1.057; (R2) & 1.058; (R3) & 1.001; (R3) & 1.008; (R3) & 1.011; (R3) &1.012; (R3) & 1.013; (R3) & 1.014; (R3) & 1.015; (R3) & 1.018; (R3) &1.019; (R3) & 1.020; (R3) & 1.021; (R3) & 1.022; (R3) & 1.054; (R3) &1.055; (R3) & 1.056; (R3) & 1.057; (R3) & 1.058; (IX) & 1.059; (IX) &1.060; (IX) & 1.061; (IX) & 1.062; (IX) & 1.063; (IX) & 1.064; (IX) &1.065; (IX) & 1.066; (IX) & 1.067; (IX) & 1.068; (IX) & 1.069; (IX) &1.070; (IX) & 1.071; (IX) & 1.072; (IX) & 1.073; (IX) & 1.074; (IX) &1.075; (IX) & 1.076; (IX) & 1.077; (IX) & 1.078; (IX) & 1.079; (IX) &1.080; (IX) & 1.081; (IX) & 1.082; (IX) & 1.083; (IX) & 1.084; (IX) &1.085; (IX) & 1.086; (IX) & 1.087; (XIII) & 1.059; (XII) & 1.060; (XIII)& 1.061; (XIII) & 1.062; (XIII) & 1.063; (XIII) & 1.064; (XIII) & 1.065;(XIII) & 1.066; (XIII) & 1.067; (XIII) & 1.068; (XIII) & 1.069; (XIII) &1.070; (XIII) & 1.071; (XIII) & 1.072; (XIII) & 1.073; (XIII) & 1.074;(XIII) & 1.075; (XIII) & 1.076; (XIII) & 1.077; (XIII) & 1.078; (XIII) &1.079; (XIII) & 1.080; (XIII) & 1.081; (XIII) & 1.082; (XIII) & 1.083;(XIII) & 1.084; (XIII) & 1.085; (XIII) & 1.086; (XIII) & 1.087; (XIV) &1.059; (XIV) & 1.060; (XIV) & 1.061; (XIV) & 1.062; (XIV) & 1.063; (XIV)& 1.064; (XIV) & 1.065; (XIV) & 1.066; (XIV) & 1.067; (XIV) & 1.068;(XIV) & 1.069; (XIV) & 1.070; (XIV) & 1.071; (XIV) & 1.072; (XIV) &1.073; (XIV) & 1.074; (XIV) & 1.075; (XIV) & 1.076; (XIV) & 1.077; (XIV)& 1.078; (XIV) & 1.079; (XIV) & 1.080; (XIV) & 1.081; (XIV) & 1.082;(XIV) & 1.083; (XIV) & 1.084; (XIV) & 1.085; (XIV) & 1.086; (XIV) &1.087; (LI) & 1.059; (LI) & 1.060; (LI) & 1.061; (LI) & 1.062; (LI) &1.063; (LI) & 1.064; (LI) & 1.065; (LI) & 1.066; (LI) & 1.067; (LI) &1.068; (LI) & 1.069; (LI) & 1.070; (LI) & 1.071; (LI) & 1.072; (LI) &1.073; (LI) & 1.074; (LI) & 1.075; (LI) & 1.076; (LI) & 1.077; (LI) &1.078; (LI) & 1.079; (LI) & 1.080; (LI) & 1.081; (LI) & 1.082; (LI) &1.083; (LI) & 1.084; (LI) & 1.085; (LI) & 1.086; (LI) & 1.087; (XXV) &1.059; (XXV) & 1.060; (XXV) & 1.061; (XXV) & 1.062; (XXV) & 1.063; (XXV)& 1.064; (XXV) & 1.065; (XXV) & 1.066; (XXV) & 1.067; (XXV) & 1.068;(XXV) & 1.069; (XXV) & 1.070; (XXV) & 1.071; (XXV) & 1.072; (XXV) &1.073; (XXV) & 1.074; (XXV) & 1.075; (XXV) & 1.076; (XXV) & 1.077; (XXV)& 1.078; (XXV) & 1.079; (XXV) & 1.080; (XXV) & 1.081; (XXV) & 1.082;(XXV) & 1.083; (XXV) & 1.084; (XXV) & 1.085; (XXV) & 1.086; (XXV) &1.087; (XXXV) & 1.059; (XXXV) & 1.060; (XXXV) & 1.061; (XXXV) & 1.062;(XXXV) & 1.063; (XXXV) & 1.064; (XXXV) & 1.065; (XXXV) & 1.066; (XXXV) &1.067, (XXXV) & 1.068; (XXXV) & 1.069; (XXXV) & 1.070; (XXXV) & 1.071;(XXXV) & 1.072; (XXXV) & 1.073; (XXXV) & 1.074; (XXXV) & 1.075; (XXXV) &1.076; (XXXV) & 1.077; (XXXV) & 1.078; (XXXV) & 1.079; (XXXV) & 1.080;(XXXV) & 1.081; (XXXV) & 1.082; (XXXV) & 1.083; (XXXV) & 1.084; (XXXV) &1.085; (XXXV) & 1.086; (XXXV) & 1.087; (XXXVIII) & 1.059; (XXXVIII) &1.060; (XXXVIII) & 1.061; (XXXVIII) & 1.062; (XXXVIII) & 1.063;(XXXVIII) & 1.064; (XXXVIII) & 1.065; (XXXVIII) & 1.066; (XXXVIII) &1.067; (XXXVIII) & 1.068; (XXXVIII) & 1.069; (XXXVIII) & 1.070;(XXXVIII) & 1.071; (XXXVIII) & 1.072; (XXXVIII) & 1.073; (XXXVIII) &1.074; (XXXVIII) & 1.075; (XXXVIII) & 1.076; (XXXVIII) & 1.077;(XXXVIII) & 1.078; (XXXVIII) & 1.079; (XXXVIII) & 1.080; (XXXVIII) &1.081; (XXXVIII) & 1.082; (XXXVIII) & 1.083; (XXXVIII) & 1.084;(XXXVIII) & 1.085; (XXXVIII) & 1.086; (XXXVIII) & 1.087; (XLI) & 1.059;(XLI) & 1.060; (XLI) & 1.061; (XLI) & 1.062; (XLI) & 1.063; (XLI) &1.064; (XLI) & 1.065; (XLI) & 1.066; (XLI) & 1.067; (XLI) & 1.068; (XLI)& 1.069; (XLI) & 1.070; (XLI) & 1.071; (XLI) & 1.072; (XLI) & 1.073;(XLI) & 1.074; (XLI) & 1.075; (XLI) & 1.076; (XLI) & 1.077; (XLI) &1.078; (XLI) & 1.079; (XLI) & 1.080; (XLI) & 1.081; (XLI) & 1.082; (XLI)& 1.083; (XLI) & 1.084; (XLI) & 1.085; (XLI) & 1.086; (XLI) & 1.087;(XLVII) & 1.059; (XLVII) & 1.060; (XLVII) & 1.061; (XLVII) & 1.062;(XLVII) & 1.063; (CIX) & 1.064; (XLVII) & 1.065; (XLVII) & 1.066;(XLVII) & 1.067; (XLVII) & 1.068; (XLVII) & 1.069; (XLVII) & 1.070;(XLVII) & 1.071; (XLVII) & 1.072; (XLVII) & 1.073; (XLVII) & 1.074;(XLVII) & 1.075; (XLVII) & 1.076; (XLVII) & 1.077; (XLVII) & 1.078;(XLVII) & 1.079; (XLVII) & 1.080; (XLVII) & 1.081; (XLVII) & 1.082;(XLVII) & 1.083; (XLVII) & 1.084; (XLVII) & 1.085; (XLVII) & 1.086;(XLVII) & 1.087; (XLIX) & 1.059; (XLIX) & 1.060; (XLIX) & 1.061; (XLIX)& 1.062; (XLIX) & 1.063; (CIX ) & 1.064; (XLIX) & 1.065; (XLIX) & 1.066;(XLIX) & 1.067; (XLIX) & 1.068; (XLIX) & 1.069; (XLIX) & 1.070; (XLIX) &1.071; (XLIX) & 1.072; (XLIX) & 1.073; (XLIX) & 1.074; (XLIX) & 1.075;(XLIX) & 1.076; (XLIX) & 1.077; (XLIX) & 1.078; (XLIX) & 1.079; (XLIX) &1.080; (XLIX) & 1.081; (XLIX) & 1.082; (XLIX) & 1.083; (XLIX) & 1.084;(XLIX) & 1.085; (XLIX) & 1.086; (XLIX) & 1.087; (LXI) & 1.059; (LXI) &1.060; (LXI) & 1.061; (LXI) & 1.062; (LXI) & 1.063; (CIX) & 1.064; (LXI)& 1.065; (LXI) & 1.066; (LXI) & 1.067; (LXI) & 1.068; (LXI) & 1.069;(LXI) & 1.070; (LXI) & 1.071; (LXI) & 1.072; (LXI) & 1.073; (LXI) &1.074; (LXI) & 1.075; (LXI) & 1.076; (LXI) & 1.077; (LXI) & 1.078; (LXI)& 1.079; (LXI) & 1.080; (LXI) & 1.081; (LXI) & 1.082; (LXI) & 1.083;(LXI) & 1.084; (LXI) & 1.085; (LXI) & 1.086; (LXI) & 1.087; (LXII) &1.059; (LXII) & 1.060; (LXII) & 1.061; (LXII) & 1.062; (LXII) & 1.063;(CIX) & 1.064; (LXII) & 1.065; (LXII) & 1.066; (LXII) & 1.067; (LXII) &1.068; (LXII) & 1.069; (LXII) & 1.070; (LXII) & 1.071; (LXII) & 1.072;(LXII) & 1.073; (LXII) & 1.074; (LXII) & 1.075; (LXII) & 1.076; (LXII) &1.077; (LXII) & 1.078; (LXII) & 1.079; (LXII) & 1.080; (LXII) & 1.081;(LXII) & 1.082; (LXII) & 1.083; (LXII) & 1.084; (LXII) & 1.085; (LXII) &1.086; (LXII) & 1.087; (CIX) & 1.059; (CIX) & 1.060; (CIX) & 1.061;(CIX) & 1.062; (CIX) & 1.063; (CIX) & 1.064; (CIX) & 1.065; (CIX) &1.066; (CIX) & 1.067; (CIX) & 1.068; (CIX) & 1.069; (CIX) & 1.070; (CIX)& 1.071; (CIX) & 1.072; (CIX) & 1.073; (CIX) & 1.074; (CIX) & 1.075;(CIX) & 1.076; (CIX) & 1.077; (CIX) & 1.078; (CIX) & 1.079; (CIX) &1.080; (CIX) & 1.081; (CIX) & 1.082; (CIX) & 1.083; (CIX) & 1.084; (CIX)& 1.085; (CIX) & 1.086; (CIX) & 1.087; (CXIII) & 1.059; (CXIII) & 1.060;(CXIII) & 1.061; (CXIII) & 1.062; (CXIII) & 1.063; (CXIII) & 1.064;(CXIII) & 1.065; (CXIII) & 1.066; (CXIII) & 1.067; (CXIII) & 1.068;(CXIII) & 1.069; (CXIII) & 1.070; (CXIII) & 1.071; (CXIII) & 1.072;(CXIII) & 1.073; (CXIII) & 1.074; (CXIII) & 1.075; (CXIII) & 1.076;(CXIII) & 1.077; (CXIII) & 1.078; (CXIII) & 1.079; (CXIII) & 1.080;(CXIII) & 1.081; (CXIII) & 1.082; (CXIII) & 1.083; (CXIII) & 1.084;(CXIII) & 1.085; (CXIII) & 1.086; (CXIII) & 1.087; (CXIX) & 1.059;(CXIX) & 1.060; (CXIX) & 1.061; (CXIX) & 1.062; (CXIX) & 1.063; (CXIX) &1.064; (CXIX) & 1.065; (CXIX) & 1.066; (CXIX) & 1.067; (CXIX) & 1.068;(CXIX) & 1.069; (CXIX) & 1.070; (CXIX) & 1.071; (CXIX) & 1.072; (CXIX) &1.073; (CXIX) & 1.074; (CXIX) & 1.075; (CXIX) & 1.076; (CXIX) & 1.077;(CXIX) & 1.078; (CXIX) & 1.079; (CXIX) & 1.080; (CXIX) & 1.081; (CXIX) &1.082; (CXIX) & 1.083; (CXIX) & 1.084; (CXIX) & 1.085; (CXIX) & 1.086;(CXIX) & 1.087; (CXXIV) & 1.059; (CXXIV) & 1.060; (CXXIV) & 1.061;(CXXIV) & 1.062; (CXXIV) & 1.063; (CXXIV) & 1.064; (CXXIV) & 1.065;(CXXIV) & 1.066; (CXXIV) & 1.067; (CXXIV) & 1.068; (CXXIV) & 1.069;(CXXIV) & 1.070; (CXXIV) & 1.071; (CXXIV) & 1.072; (CXXIV) & 1.073;(CXXIV) & 1.074; (CXXIV) & 1.075; (CXXIV) & 1.076; (CXXIV) & 1.077;(CXXIV) & 1.078; (CXXIV) & 1.079; (CXXIV) & 1.080; (CXXIV) & 1.081;(CXXIV) & 1.082; (CXXIV) & 1.083; (CXXIV) & 1.084; (CXXIV) & 1.085;(CXXIV) & 1.086; (CXXIV) & 1.087; (CXXXI) & 1.059; (CXXXI) & 1.060;(CXXXI) & 1.061; (CXXXI) & 1.062; (CXXXI) & 1.063; (CXXXI) & 1.064;(CXXXI) & 1.065; (CXXXI) & 1.066; (CXXXI) & 1.067; (CXXXI) & 1.068;(CXXXI) & 1.069; (CXXXI) & 1.070; (CXXXI) & 1.071; (CXXXI) & 1.072;(CXXXI) & 1.073; (CXXXI) & 1.074; (CXXXI) & 1.075; (CXXXI) & 1.076;(CXXXI) & 1.077; (CXXXI) & 1.078; (CXXXI) & 1.079; (CXXXI) & 1.080;(CXXXI) & 1.081; (CXXXI) & 1.082; (CXXXI) & 1.083; (CXXXI) & 1.084;(CXXXI) & 1.085; (CXXXI) & 1.086; (CXXXI) & 1.087; (CXXXII) & 1.059;(CXXXII) & 1.060; (CXXXII) & 1.061; (CXXXII) & 1.062; (CXXXII) & 1.063;(CXXXII) & 1.064; (CXXXII) & 1.065; (CXXXII) & 1.066; (CXXXII) & 1.067;(CXXXII) & 1.068; (CXXXII) & 1.069; (CXXXII) & 1.070; (CXXXII) & 1.071;(CXXXII) & 1.072; (CXXXII) & 1.073; (CXXXII) & 1.074; (CXXXII) & 1.075;(CXXXII) & 1.076; (CXXXII) & 1.077; (CXXXII) & 1.078; (CXXXII) & 1.079;(CXXXII) & 1.080; (CXXXII) & 1.081; (CXXXII) & 1.082; (CXXXII) & 1.083;(CXXXII) & 1.084; (CXXXII) & 1.085; (CXXXII) & 1.086; (CXXXII) & 1.087;(CXXXIX) & 1.059; (CXXXIX) & 1.060; (CXXXIX) & 1.061; (CXXXIX) & 1.062;(CXXXIX) & 1.063; (CXXXIX) & 1.064; (CXXXIX) & 1.065; (CXXXIX) & 1.066;(CXXXIX) & 1.067; (CXXXIX) & 1.068; (CXXXIX) & 1.069; (CXXXIX) & 1.070;(CXXXIX) & 1.071; (CXXXIX) & 1.072; (CXXXIX) & 1.073; (CXXXIX) & 1.074;(CXXXIX) & 1.075; (CXXXIX) & 1.076; (CXXXIX) & 1.077; (CXXXIX) & 1.078;(CXXXIX) & 1.079; (CXXXIX) & 1.080; (CXXXIX) & 1.081; (CXXXIX) & 1.082;(CXXXIX) & 1.083; (CXXXIX) & 1.084; (CXXXIX) & 1.085; (CXXXIX) & 1.086;(CXXXIX) & 1.087; (A1) & 1.059; (A1) & 1.060; (A1) & 1.061; (A1) &1.062; (A1) & 1.063; (A1) & 1.064; (A1) & 1.065; (A1) & 1.066; (A1) &1.067; (A1) & 1.068; (A1) & 1.069; (A1) & 1.070; (A1) & 1.071; (A1) &1.072; (A1) & 1.073; (A1) & 1.074; (A1) & 1.075; (A1) & 1.076; (A1) &1.077; (A1) & 1.078; (A1) & 1.079; (A1) & 1.080; (A1) & 1.081; (A1) &1.082; (A1) & 1.083; (A1) & 1.084; (A1) & 1.085; (A1) & 1.086; (A1) &1.087; (A2) & 1.059; (A2) & 1.060; (A2) & 1.061; (A2) & 1.062; (A2) &1.063; (A2) & 1.064; (A2) & 1.065; (A2) & 1.066; (A2) & 1.067; (A2) &1.068; (A2) & 1.069; (A2) & 1.070; (A2) & 1.071; (A2) & 1.072; (A2) &1.073; (A2) & 1.074; (A2) & 1.075; (A2) & 1.076; (A2) & 1.077; (A2) &1.078; (A2) & 1.079; (A2) & 1.080; (A2) & 1.081; (A2) & 1.082; (A2) &1.083; (A2) & 1.084; (A2) & 1.085; (A2) & 1.086; (A2) & 1.087; (A3) &1.059; (A3) & 1.060; (A3) & 1.061; (A3) & 1.062; (A3) & 1.063; (A3) &1.064; (A3) & 1.065; (A3) & 1.066; (A3) & 1.067; (A3) & 1.068; (A3) &1.069; (A3) & 1.070; (A3) & 1.071; (A3) & 1.072; (A3) & 1.073; (A3) &1.074; (A3) & 1.075; (A3) & 1.076; (A3) & 1.077; (A3) & 1.078; (A3) &1.079; (A3) & 1.080; (A3) & 1.081; (A3) & 1.082; (A3) & 1.083; (A3) &1.084; (A3) & 1.085; (A3) & 1.086; (A3) & 1.087; (A4) & 1.059; (A4) &1.060; (A4) & 1.061; (A4) & 1.062; (A4) & 1.063; (A4) & 1.064; (A4) &1.065; (A4) & 1.066; (A4) & 1.067; (A4) & 1.068; (A4) & 1.069; (A4) &1.070; (A4) & 1.071; (A4) & 1.072; (A4) & 1.073; (A4) & 1.074; (A4) &1.075; (A4) & 1.076; (A4) & 1.077; (A4) & 1.078; (A4) & 1.079; (A4) &1.080; (A4) & 1.081; (A4) & 1.082; (A4) & 1.083; (A4) & 1.084; (A4) &1.085; (A4) & 1.086; (A4) & 1.087; (A6) & 1.059; (A6) & 1.060; (A6) &1.061; (A6) & 1.062; (A6) & 1.063; (A6) & 1.064; (A6) & 1.065; (A6) &1.066; (A6) & 1.067; (A6) & 1.068; (A6) & 1.069; (A6) & 1.070; (A6) &1.071; (A6) & 1.072; (A6) & 1.073; (A6) & 1.074; (A6) & 1.075; (A6) &1.076; (A6) & 1.077; (A6) & 1.078; (A6) & 1.079; (A6) & 1.080; (A6) &1.081; (A6) & 1.082; (A6) & 1.083; (A6) & 1.084; (A6) & 1.085; (A6) &1.086; (A6) & 1.087; (R2) & 1.059; (R2) & 1.060; (R2) & 1.061; (R2) &1.062; (R2) & 1.063; (R2) & 1.064; (R2) & 1.065; (R2) & 1.066; (R2) &1.067; (R2) & 1.068; (R2) & 1.069; (R2) & 1.070; (R2) & 1.071; (R2) &1.072; (R2) & 1.073; (R2) & 1.074; (R2) & 1.075; (R2) & 1.076; (R2) &1.077; (R2) & 1.078; (R2) & 1.079; (R2) & 1.080; (R2) & 1.081; (R2) &1.082; (R2) & 1.083; (R2) & 1.084; (R2) & 1.085; (R2) & 1.086; and (R2)& 1.087, preference being given to those combinations in which a partneris underlined.

The following reaction scheme gives a diagrammatic overview of thepreparation of the compounds of formula (I):

wherein

the substituents R, R₁, R₂, R₂′, X, Y, T and U indicated in the abovescheme are as defined for formula (I);

W is a leaving group; and

Hal is halogen, such as fluorine, chlorine, bromine or iodine,preferably chlorine, bromine or iodine.

Leaving groups W in the compounds of formulae (VI) and (VIII) that aresuitable for the reactions are known from the literature and aredescribed, e.g., in Houben-Weyl-Methoden der organischen Chemie, Vol.E4-carbonic acid derivatives, pp. 149-165; Hagemann, Eds., Georg ThiemeVerlag, Stuttgart (1983). Especially preferred leaving groups arehalogen, preferably iodine or chlorine; C₁-C₈alkoxy, C₁-C₈alkylthio,phenoxy, N-hydroxy-succinimide, N-hydroxy-phthalimide, imidazole,triazoles and 1-hydroxybenzotriazole-N-oxyl. It will be understood thatall leaving groups that contain aliphatic or aromatic rings may beunsubstituted or substituted at those rings by customary substituents.

The compounds of formula (XX) are novel except of1-(1-chloroethoxycarbonyl)-3-(2-chloro-5-thiatolylmethyl)-1-methyl-2-nitroguanidin,which is described in EP 0 471 371 and in JP-A-05 11251. They exhibit apesticidal spectrum of action similar to that of the compounds offormula (I). The present invention relates to those compounds also. Inthe compounds of formula (XX), as regards the substituents R₁, R₂, R₂′,X, Y, T and U preference is given to the same substituents as thosealready mentioned for the preferred sub-groups of compounds of formula(I), Hal preferably being fluorine or chlorine, especially chlorine. Asa result of the Hal substituent, these novel compounds are excellentlysuitable for further derivatisation and therefore for the preparation ofparasiticides, for example, the compounds of formula (I).

The reactions illustrated and described hereinabove and hereinbelow arecarried out in a manner known per se, for example, in the absence or,usually, in the presence of a suitable solvent or diluent or a mixturethereof, the operation being carried out, as required, with cooling, atroom temperature or with heating, for example in a temperature range offrom about −80° C. to the boiling temperature of the reaction medium,preferably from about −40° C. to about +120° C., especially from −20° C.to 40° C. and, if necessary, in a closed vessel, under pressure, in aninert gas atmosphere and/or under anhydrous conditions. Especiallyadvantageous reaction conditions for each individual reaction step canbe found in the explanations which follow and in the specificPreparation Examples.

Unless special conditions are mentioned, the reactants can in principlebe reacted with one another as such, that is to say without the additionof a solvent or diluent, for example, in the molten state. It is moreadvantageous, however, to add an inert solvent or diluent or a mixturethereof. Examples of such solvents or diluents that may be mentionedinclude aromatic, aliphatic and alicyclic hydrocarbons and halogenatedhydrocarbons, such as benzene, toluene, xylene, mesitylene, Tetralin,chlorobenzene, dichlorobenzene, bromobenzene, petroleum ether, hexane,cyclohexane, dichloromethane, trichloromethane, tetrachloromethane,dichloroethane, trichloroethene or tetrachloroethene; esters, such asethyl acetate; ethers, such as diethyl ether, dipropyl ether,diisopropyl ether, dibutyl ether, tert-butyl methyl ether, ethyleneglycol monomethyl ether, ethylene glycol monoethyl ether, ethyleneglycol dimethyl ether, dimethoxydiethyl ether, tetrahydrofuran ordioxane; ketones, such as acetone, methyl ethyl ketone or methylisobutyl ketone; alcohols, such as methanol, ethanol, propanol,isopropanol, butanol, ethylene glycol or glycerol; amides, such asN,N-dimethylformamide, N,N-diethylformamide, N,N-dimethylacetamide,N-methylpyrrolidone or hexamethylphosphoric acid triamide; nitriles,such as acetonitrile or propionitrile; and sulfoxides, such as dimethylsulfoxide. If the reaction in question is carried out in the presence ofa base, bases used in excess, such as triethylamine, pyridine,N-methylmorpholine or N,N-diethylaniline, may also serve as solvent ordiluent. If the reaction is carried out in the presence of an acidcatalyst, it is also possible to employ as solvent or diluent acids usedin excess, e.g., strong organic carboxylic acids, such as unsubstitutedor substituted, e.g., halo-substituted, C₁-C₄alkanecarboxylic acids,e.g., formic acid, acetic acid or propionic acid. Suitable solvents forthe reaction in question can be taken from the Examples given below.

Bases suitable for facilitating those reactions in which base catalystsmay optionally be used are, e.g., alkali metal or alkaline earth metalhydroxides, hydrides, alkylides, amides, alkanolates, acetates,carbonates, dialkylamides or alkylsilylamides; alkylamines,alkylenediamines, free or N-alkylated, saturated or unsaturatedcycloalkylamines, basic heterocycles, ammonium hydroxides and alsocarbocyclic amines. Examples are butyllithium, sodium hydroxide, sodiumhydride, sodium amide, sodium methanolate, sodium acetate, sodiumcarbonate, potassium tert-butanolate, potassium hydroxide, potassiumcarbonate, potassium hydride, lithium diisopropylamide, potassiumbis(trimethylsilyl)amide, calcium hydride, triethylamine,diisopropylethylamine, triethylenediamine, cyclohexylamine,N-cyclohexyl-N,N-dimethylamine, N,N-diethylaniline, pyridine,4-(N,N-dimethylamino)pyridine, quinuclidine, N-methylmorpholine,benzyltrimethylammonium hydroxide and also1,5-diazabicyclo[5.4.0]undec-5-ene (DBU). For replacing chlorine byiodine in a compound of formula (VI), the base used is preferably silvercarbonate and the reagent used sodium iodide.

The procedure in detail is as follows: the compounds of formula (I) areprepared by either (a) reacting a compound of formula (IX) in anaprotic, advantageously polar, solvent in the presence of a suitablebase and at relatively low temperatures with a compound of formula (VII)or preferably (b) reacting a compound of formula (XX) with an acid RCOOHand isolating the end product from the reaction mixture, thesubstituents R, R₁, R₂, R₂′, X, Y, T and U being as defined for formula(I); W being a leaving group; and Hal being halogen, such as fluorine,chlorine, bromine or iodine, preferably chlorine, bromine or iodine. Thereaction is advantageously carried out in an anhydrous medium and underan inert gas atmosphere, e.g., under nitrogen or argon. The saidreactions take place within a period of minutes up to several hours.

A preferred embodiment comprises the following features: the compound offormula (IX) is first dissolved in an anhydrous, aprotic, polar solvent,and then at a relatively low temperature, for example, at ambienttemperature or lower, an equimolar amount of one of the suitable basesdescribed above, for example, sodium hydride, is added and the mixtureis stirred for a little longer at the same temperature. An equimolaramount of the compound of formula (VIII) dissolved in the same solventis then added in portions, e.g., by dropwise addition, and stirring ofthe reaction mixture is continued at the same low temperature for alittle longer. Any excess base is then neutralized and the reactionmixture is stirred for a few minutes longer and finally concentrated.The residue is advantageously taken up in a polar solvent, such as ethylacetate, and optionally washed with water, and the organic phase isseparated off and dried over a drying agent, e.g., an alkali or alkalineearth metal sulfate or carbonate, preferably magnesium or sodiumsulfate, concentrated and purified. A suitable purification step ischromatography, e.g., on silica gel (ethyl acetate:hexane/1:1).Compounds of formula (I) are generally obtained in the form ofcolourless to dark yellow oils, resins or in the form of solids. Thesaid oils and resins crystallise after a few days or weeks when stored,e.g., in a freezer at about from −18° to −25° C.

In the context of the present invention, relatively low temperatures areto be understood as being temperatures around room temperature and belowor a temperature range of from about +25° C. to about −80° C.,preferably from room temperature to about −20° C.

The compounds of formula (IX) are known per se from the literature orcan be prepared analogously to the examples described in the literature.For example, compounds of formula (IX) wherein Het is pyridyl that isunsubstituted or mono- or poly-substituted by halogen are described,together with their preparation, in European published specification EP0 302 833. Further compounds of formula (IX) are disclosed in thefollowing patent references, e.g., in European published specificationsNos. 285 985; 302 389, 376 279, 471 372, 364 844, 493 369, 381 130, 529680, 163 855, 375 907, 259 738, 386 565, 383 091 and 590 425; U.S. Pat.Nos. 5,063,236, 5,302,605 and 4,742,060; and also in DE 4 207 604; GB 2228 003 and WO 93/24002.

The compounds of formula (VIII) wherein R, R₂ and R₂′ are as defined forformula (I) and W is one of the leaving groups mentioned above can beprepared by introducing the radical RCOO— into a compound of formula(VI). For that purpose it is advantageous to prepare a suspension of acompound of formula (VI), wherein Hal is iodine and an organic acidR—COOH, an example of which is benzoic acid, and silver carbonate in anaprotic solvent, e.g., toluene or xylene. The suspension is heated atfrom about 50° C. to about 100° C. for a few hours and then the reactionmixture is cooled to room temperature and insoluble constituents arefiltered off. The filtrate is washed with water and/or aqueous sodiumchloride solution and dried over a customary drying agent, such asmagnesium or sodium sulfate. On concentration, the compound of formula(VIII) is obtained in the form of an oil or a crystalline solid. It isgenerally unnecessary to carry out further purification before use inthe next reaction step.

The preparation of compounds of formula (VI), wherein

R₂ and R₂′ are as defined for formula (I);

W is one of the leaving groups mentioned hereinabove; and

Hal is iodine is effected by replacing by iodine the chlorine atom in acompound of formula (VI), wherein Hal is chlorine.

For this purpose a suspension of the compound of formula (VI) whereinHal is chlorine, an equimolar amount of sodium iodide and sodiumhydrogen carbonate in a polar solvent, such as acetone, is prepared andis stirred at slightly elevated temperature, about 40° C., for from12-24 hours. The resulting precipitate is filtered off and washed withacetone. The filtrate is concentrated, and diethyl ether and water areadded. The organic phase is separated off and washed with aqueouspotassium sulfite solution, then washed with aqueous sodium chloridesolution and dried over a customary drying agent, such as magnesium orsodium sulfate. On concentration, the compound of formula (VI) isobtained in the form of a colourless, crystalline product, which can befiltered off and freed of solvent residues, e.g., in vacuo. Furtherpurification before use in the next reaction step is unnecessary.

Compounds of formula (VI) can be prepared by dissolving compounds offormula (VI), wherein R₂ and R₂′ are as defined for formula (I) and W ischlorine in a halogenated solvent, such as dichloromethane, and at lowtemperature, advantageously about 0° C., adding a solution of a compoundof the formula H—W in portions and then stirring the reaction mixture atthe low temperature for about 1-3 hours. Water is then added and theorganic phase is separated off, washed with 1 N sodium hydroxidesolution and then with aqueous sodium chloride solution and dried over adrying agent, e.g., magnesium sulfate. On concentration, the compound offormula (VI) is obtained in the form of a colorless, crystallineproduct, which can be filtered off and freed of solvent residues invacuo.

As illustrated in the above reaction scheme, the novel compounds offormula (XX) are prepared by reacting a compound of formula (IX) in anaprotic, advantageously polar, solvent in the presence of a suitablebase and at relatively low temperatures, with a compound of formula(VI), the substituents R₁, R₂, R₂′, X, Y, T and U in the formulae (XX),(IX) and (VI) being as defined for formula (I); W being a leaving group;and Hal being halogen, such as fluorine, chlorine, bromine or iodine andpreferably chlorine or iodine. The compound of formula (IX) is firstdissolved in an anhydrous, aprotic, polar solvent, and then atrelatively low temperature, e.g., ambient temperature or lower, anequimolar amount of one of the suitable bases described above, e.g.,sodium hydride, is added and the mixture is stirred for a little longerat the same temperature. An equimolar amount of the compound of formula(VI) dissolved in the same solvent is then added in portions, e.g., bydropwise addition, and stirring of the reaction mixture is continued atthe same low temperature for a little longer. Any excess base is thenneutralised and the reaction mixture is stirred for a few minutes longerand finally concentrated. The residue is advantageously taken up in apolar solvent, such as ethyl acetate, and optionally washed with water,and the organic phase is separated off and dried over a drying agent,e.g., an alkali or alkaline earth metal sulfate or carbonate, preferablymagnesium or sodium sulfate, concentrated and purified. A suitablepurification step is chromatography, e.g., on silica gel (ethylacetate:hexane/1:1). Compounds of formula (XX) are generally obtained inthe form of colorless to dark yellow oils, resins or, predominantly, inthe form of solids.

PREPARATION EXAMPLES Preparation of Preliminary Products

Preparation of carbonic acid (chloromethyl ester) (4-nitrophenyl ester):

At 0° C., a solution of 69.6 g of 4-nitrophenol and 39.6 g of pyridinein 500 mL of dichloromethane is added dropwise in the course of 30minutes to a solution of 71 g of chloromethyl chloroformate in 1000 mLof dichloromethane. The reaction mixture is stirred at 0° C. for afurther 2 hours and then 1000 mL of H₂O are added. The organic phase iswashed using 250 mL each of 1 N NaOH and aqueous sodium chloridesolution and dried over MgSO₄. After concentration of the solvent, 111 gof a white solid having a melting point of 61-62° C. are obtained.

Preparation of carbonic acid (iodomethyl ester) (4-nitrophenyl ester)

34.8 g of carbonic acid (chloromethyl ester) (4-nitrophenyl ester), 45.0g of NaI and 2.52 g of NaHCO₃ are suspended in 350 mL of acetone and theresulting suspension is stirred at a temperature of 40° C. for 16 hours.The precipitate is filtered off and washed with 100 mL of acetone. Thefiltrate is concentrated and the residue is taken up in 500 mL ofdiethyl ether and 100 mL of H₂O. The organic phase is washed with 100 mLeach of saturated potassium disulfite solution and aqueous sodiumchloride solution, dried over MgSO₄ and concentrated. 47.4 g of a whitesolid having a melting point of 45-46° C. are obtained.

Preparation of benzoic acid 4-nitrophenoxycarbonyloxymethyl ester

0.97 g of carbonic acid (iodomethyl ester) (4-nitrophenyl ester), 0.55 gof benzoic acid and 1.24 g of Ag₂CO₃ are suspended in 30 mL of tolueneand stirred at 80° C. for 3 hours. The mixture is cooled to roomtemperature and the precipitate is filtered off. The filtrate is washedwith 15 mL each of H₂O and aqueous sodium chloride solution, dried overMgSO₄ and concentrated. 0.75 g of the desired product is obtained in theform of a white solid having a melting point of 69-71° C.

Preparation of carbonic acid (chloromethyl ester) (N-hydroxysuccinimideester)

At 0° C., a solution of 99.3 g of N-hydroxysuccinimide and 55.4 g ofpyridine in 250 mL of dichloromethane is added in the course of 60minutes to a solution of 80.6 g of chloromethyl chloroformate in 750 mLof dichloromethane. The reaction mixture is stirred at 0° C. for afurther 5 hours and then 1000 mL of H₂O are added. The organic phase iswashed with 250 mL each of 1 N NaOH and aqueous sodium chloride solutionand dried over MgSO₄. After concentration of the solvent, 119 g of awhite solid having a melting point of 103-105° C. are obtained.

Preparation of{1-[(6-chloro-pyridin-3-ylmethyl)-ethyl-amino]-2-nitro-vinyl}-methyl-carbamicacid) chloromethyl ester

6.35 g of sodium hydride are added in portions at 0° C. under a N₂atmosphere to a solution of 65 g ofN-(6-chloro-pyridin-3-ylmethyl)-N-ethyl-N′-methyl]-2-nitro-vinylidenediaminein 300 mL of DMF. The mixture is stirred at 0° C. for 1 hour and then,at −20° C., 50 g of carbonic acid (chloromethyl ester)(N-hydroxysuccinimide ester) dissolved in 200 mL of DMF are addeddropwise thereto. After 1 hour at −20° C., 250 mL of saturated NH₄Clsolution and 300 mL of ethyl acetate are added. The organic phase isseparated off and washed with 300 mL of 1 N NaOH, 300 mL of water and300 mL of saturated sodium chloride solution. After drying over MgSO₄,the solvent system is concentrated and the residue is stirred at refluxtemperature with 300 mL of MeOH. After cooling to room temperature, 33.5g of whitish-yellow crystals having a melting point of 142-143° C. areobtained.

Preparation of End Products

Preparation of benzoic acid({1-[(6-chloro-pyridin-3-ylmethyl)-ethyl-amino]-2-nitro-vinyl}-methyl-carbamoyloxy)-methylester

Under a N₂ atmosphere, 53 mg of NaH are added to a solution of 270 mg ofN-(6-chloro-pyridin-3-ylmethyl)-N-ethyl-N′-methyl]-2-nitro-vinylidenediaminein 20 mL of DMF. The mixture is stirred at room temperature for 1 hour.Then, at −20° C., 635 mg of benzoic acid4-nitro-phenoxycarbonyloxymethyl ester dissolved in 5 mL of DMF areadded dropwise. After 6 hours at −20° C., 1 mL of saturated NH₄Clsolution is added and the solvent system is concentrated. The residue istaken up in 50 mL of ethyl acetate and washed with 25 mL of H₂O. Theorganic phase is dried over MgSO₄ and concentrated, and the residue ischromatographed on silica gel (ethyl acetate:hexane; 1:1). 450 mg ofwhitish-yellow crystals having a melting point of 62-63° C. areobtained.

Preparation of 2,2-dimethylbutyric acid{1-[(6-Chloro-pyridin-3-ylmethyl)-ethyl-amino]-2-nitro-vinyl}-methyl-carbamoyloxy)-methylester

A mixture of 10.9 g of{1-[(6-chloro-pyridin-3-ylmethyl)-ethyl-amino]-2-nitro-vinyl}-methyl-carbamicacid chloromethyl ester, 4.18 g of 2,2-dimethylbutyric acid and 5.39 gof potassium carbonate in 125 mL of DMF is stirred at a temperature of50° C. for 12 hours. The mixture is cooled to room temperature, theprecipitate is filtered off and 250 mL of diethyl ether and 250 mL of 1N NaOH are added to the filtrate. The organic phase is separated off andwashed with 250 mL of water and 250 mL of saturated sodium chloridesolution. After drying over MgSO₄, the solvent system is concentratedand the residue is stirred with 200 mL of diethyl ether and 100 mL ofhexane. 11.1 g of white crystals having a melting point of 79-80° C. areobtained.

In an analogous manner it is also possible to prepare the followingtypical compounds listed in the Table.

Typical compounds of formula (I) are listed in Tables 1-4, while Tables5-8 give typical examples of intermediates of formula (XX). The presentinvention is not limited to the typical examples shown, however.

TABLE 1 Compounds of formula (Xa)

No. M L T U R₂ R₂′ R Physical Data 1.001 6-Cl H C₂H₅ CH₃ H H CH₃ yellowresin 1.002 6-Cl 5-Cl C₂H₅ CH₃ H H CH₃ 1.003 6-Cl H CH₃ CH₃ H H CH₃1.004 6-Cl H C₂H₅ CH₃ CH₃ H CH₃ 1.005 6-Cl H C₂H₅ CH₃ H H C₂H₅ 1.0066-Cl H C₂H₅ CH₃ H H i-C₃H₇ 1.007 6-Cl H C₂H₅ CH₃ H H n-C₃H₇ 1.008 6-Cl HC₂H₅ CH₃ H H n-C₄H₉ m.p. 66-68° C. 1.009 6-Cl H H CH₃ H H s-C₄H₉ 1.010 H5-Cl C₂H₅ CH₃ H H t-C₄H₉ 1.011 6-Cl H C₂H₅ CH₃ H H n-C₇H₁₅ m.p. 84-85°C. 1.012 6-Cl H C₂H₅ CH₃ H H n-C₁₁H₂₃ yellow resin 1.013 6-Cl H C₂H₅ CH₃H H n-C₁₃H₂₇ m.p. 52-54° C. 1.014 6-Cl H C₂H₅ CH₃ H H n-C₁₅H₃₁ m.p.56-58° C. 1.015 6-Cl H C₂H₅ CH₃ H H n-C₁₇H₃₅ m.p. 60-61° C. 1.016 6-Cl5-Cl C₂H₅ CH₃ H H n-C₁₁H₂₃ 1.017 6-Cl 5-F CH₃ CH₃ H H n-C₇H₁₅ 1.018 6-ClH C₂H₅ CH₃ H H phenyl glassy m.p. 62-63° C. 1.019 6-Cl H C₂H₅ CH₃ H Hn-C₅H₁₁ resin 1.020 6-Cl H C₂H₅ CH₃ H H biphenyl glassy m.p. 72-69° C.1.021 6-Cl H C₂H₅ CH₃ H H phenoxyphenyl glassy m.p. 60-61° C. 1.022 6-ClH C₂H₅ CH₃ H H 4-t-butyl-phenyl glassy m.p. 103-5° C. 1.023 6-Cl H C₂H₅CH₃ H H 2-chloro-phenyl 1.024 6-Cl H C₂H₅ CH₃ H H 2,6-difluoro-phenyl1.025 6-Cl H C₂H₅ H H H n-C₁₇H₃₅ 1.026 6-Cl H C₂H₅ C₂H₅ CH₃ H n-C₇H₁₅1.027 6-Cl H C₂H₅ CH₃ C₂H₅ H CH₃ 1.028 6-Cl H C₂H₅ CH₃ n-C₃H₇ H CH₃1.029 6-Cl H C₂H₅ CH₃ s-C₄H₉ H CH₃ 1.030 6-Cl H C₂H₅ CH₃ n-C₆H₁₃ H CH₃1.031 6-Cl H CH₃ CH₃ CH₃ H CH₃ 1.032 6-Cl 4-F CH₃ CH₃ CH₃ H CH₃ 1.0336-Cl H C₂H₅ CH₃ H H cyclohexyl 1.034 6-Cl H C₂H₅ CH₃ H H vinyl 1.0356-Cl H C₂H₅ CH₃ H H allyl 1.036 6-Cl H C₂H₅ CH₃ H H 2-propargyl 1.0376-Cl H C₂H₅ CH₃ CH₃ CH₃ CH₃ 1.038 6-Cl H C₂H₅ CH₃ CH₃ CH₃ n-C₄H₉ 1.0396-Cl H C₂H₅ CH₃ CH₃ CH₃ n-C₇H₁₅ 1.040 6-Cl H C₂H₅ CH₃ C₂H₅ CH₃ n-C₁₁H₂₃1.041 6-Cl H C₂H₅ CH₃ CH₃ CH₃ n-C₁₃H₂₇ 1.042 6-Cl H C₂H₅ CH₃ C₂H₅ C₂H₅n-C₁₅H₃₁ 1.043 6-Cl H C₂H₅ CH₃ n-C₃H₇ C₂H₅ n-C₁₇H₃₅ 1.044 6-Cl H C₂H₅CH₃ CH₃ s-C₄H₉ phenyl 1.045 6-Cl H C₂H₅ CH₃ CH₃ n-C₃H₇ biphenyl 1.0466-Cl H C₂H₅ CH₃ s-C₄H₉ C₂H₅ phenoxyphenyl 1.047 6-Cl H C₂H₅ CH₃ s-C₄H₉C₂H₅ 4-s-butyl-phenyl 1.048 6-Cl H C₂H₅ CH₃ s-C₄H₉ n-C₃H₇2-fluoro-phenyl 1.049 6-Cl H C₂H₅ C₂H₅ CH₃ n-C₃H₇ n-C₇H₁₅ 1.050 6-Cl HC₂H₅ CH₃ C₂H₅ CH₃ CH₃ 1.051 6-Cl H C₂H₅ CH₃ n-C₃H₇ CH₃ CH₃ 1.052 6-Cl HC₂H₅ CH₃ s-C₄H₉ CH₃ CH₃ 1.053 6-Cl H C₂H₅ CH₃ n-C₆H₁₃ H CH₃ 1.054 6-Cl HC₂H₅ CH₃ H H C(CH₃)₂C₃H₇-n m.p. 73-74° C. 1.055 6-Cl H C₂H₅ CH₃ H HC(CH₃)₂C₃H₇-n m.p. 92-93° C. 1.056 6-Cl H C₂H₅ CH₃ H H C(CH₃)₂C₂H₅ m.p.79-80° C. 1.057 6-Cl H C₂H₅ CH₃ H H n-C₆H₁₃ m.p. 84-85° C. 1.058 6-Cl HC₂H₅ CH₃ H H n-C₁₀H₂₁ resin 1.059 6-Cl H C₂H₅ CH₃ H H CH(CH₃)C₃H₇n m.p73-74° C. 1.060 6-Cl H C₂H₅ CH₃ H H n-C₅H₁₁ oil 1.061 6-Cl H C₂H₅ CH₃ HH n-C₈H₁₇ m.p. 53-55° C. 1.062 6-Cl H C₂H₅ CH₃ H H n-C₄H₉ oil 1.063 6-ClH C₂H₅ CH₃ H H 1-phenyl-1-cyclo- m.p. 101-103° C. pentyl 1.064 6-Cl HC₂H₅ CH₃ H H 1-phenyl-1-cyclo- glass propyl 1.065 6-Cl H C₂H₅ CH₃ H H1-phenyl-1-cyclo-hexyl m.p. 110-112° C. 1.066 6-Cl H C₂H₅ CH₃ H HC(CH₃)₂phenyl m.p. 104-105° C. 1.067 6-Cl H C₂H₅ CH₃ H H2,6-dimethylphenyl m.p. 108-111° C. 1.068 6-Cl H C₂H₅ CH₃ H H2,4,6-tri-isopropyl- m.p. 118-119° C. phenyl 1.069 6-Cl H C₂H₅ CH₃ H Hcyclohexyl m.p. 94-96° C. 1.070 6-Cl H C₂H₅ CH₃ H H benzyl glass 1.0716-Cl H C₂H₅ CH₃ H H 1-adamantyl m.p. 158-160° C. 1.072 6-Cl H C₂H₅ CH₃ HH t-C₄H₉ m.p. 136-137° C. 1.073 6-Cl H C₂H₅ CH₃ H H CH(phenyl)₂ glass1.074 6-Cl H C₂H₅ CH₃ H H cyclopropyl m.p. 112-113° C. 1.075 6-Cl H C₂H₅CH₃ H H CH(C₂H₅)₂ m.p. 69-70° C. 1.076 6-Cl H C₂H₅ CH₃ H H CH(n-C₃H₇)₂m.p. 81-82° C. 1.077 6-Cl H C₂H₅ CH₃ H H CH₂(cyclohexyl) m.p. 71-73° C.1.078 6-Cl H C₂H₅ CH₃ H H CH₂CH₂(cyclo-hexyl) m.p. 91-93° C. 1.079 6-ClH C₂H₅ CH₃ H H 3-(t-C₄H₉)cyclo-hex-1- m.p. 107-110° C. yl 1.080 6-Cl HC₂H₅ CH₃ H H 1-(4-chloro-phenyl)-1- m.p. 125-126° C. cyclopentyl 1.0816-Cl H C₂H₅ CH₃ H H 1-(4-fluoro-phenyl)-1- m.p. 105-107° C. cyclopentyl1.082 6-Cl H C₂H₅ CH₃ H H CH₂C(CH₃)₂CH₃ m.p. 107-108° C. 1.083 6-Cl HC₂H₅ CH₃ H H CH₂CH(phenyl)₂ m.p. 91-93° C. 1.084 6-Cl H C₂H₅ CH₃ H H1-methyl-2,2-di-chloro- m.p. 80-82° C. 1 -cyclopropyl 1.085 6-Cl H C₂H₅CH₃ H H 1-methyl-1-cyclohexyl m.p. 95-96° C. 1.086 6-Cl H C₂H₅ CH₃ H Hcyclopentyl m.p. 134-135° C. 1.087 6-Cl H C₂H₅ CH₃ CH₃ CH₃ 4-Cl-phenylglass 1.088 6-Cl H CH₃ CH₃ CH₃ CH₃ CH₃ 1.089 6-Cl 5-Cl CH₃ CH₃ H H CH₃1.090 6-Cl H CH₃ CH₃ H H CH₃ 1.091 6-Cl H CH₃ CH₃ CH₃ H CH₃ 1.092 6-Cl HCH₃ CH₃ H H C₂H₅ 1.093 6-Cl H CH₃ CH₃ H H i-C₃H₇ 1.094 6-Cl H CH₃ CH₃ HH n-C₃H₇ 1.095 6-Cl H CH₃ CH₃ H H n-C₄H₉ 1.096 6-Cl H CH₃ CH₃ H H s-C₄H₉1.097 H 5-Cl CH₃ CH₃ H H t-C₄H₉ 1.098 6-Cl H CH₃ CH₃ H H n-C₇H₁₅ 1.0996-Cl H CH₃ CH₃ H H n-C₁₁H₂₃ 1.100 6-Cl H CH₃ CH₃ H H n-C₁₃H₂₇ 1.101 6-ClH CH₃ CH₃ H H n-C₁₅H₃₁ 1.102 6-Cl H CH₃ CH₃ H H n-C₁₇H₃₅ 1.103 6-Cl 5-ClCH₃ CH₃ H H n-C₁₁H₂₃ 1.104 6-Cl 5-F CH₃ CH₃ CH₃ CH₃ n-C₇H₁₅ 1.105 6-Cl HCH₃ CH₃ H H phenyl 1.106 6-Cl H CH₃ CH₃ H H n-C₅H₁₁ 1.107 6-Cl H CH₃ CH₃H H biphenyl 1.108 6-Cl H CH₃ CH₃ H H phenoxyphenyl 1.109 6-Cl H CH₃ CH₃H H 4-t-butyl-phenyl 1.110 6-Cl H CH₃ CH₃ H H 2-chloro-phenyl 1.111 6-ClH CH₃ CH₃ H H 2,6-difluoro-phenyl 1.112 6-Cl H CH₃ CH₃ H H C(CH₃)₂C₃H₇-n1.113 6-Cl H CH₃ CH₃ H H C(CH₃)₂C₃H₇-n 1.114 6-Cl H CH₃ CH₃ H HC(CH₃)₂C₂H₅ 1.115 6-Cl H CH₃ CH₃ H H n-C₆H₁₃ 1.116 6-Cl H CH₃ CH₃ H Hn-C₁₀H₂₁ 1.117 6-Cl H CH₃ CH₃ H H CH(CH₃)C₃H₇n 1.118 6-Cl H CH₃ CH₃ H Hn-C₅H₁₁ 1.119 6-Cl H CH₃ CH₃ H H n-C₈H₁₇ 1.120 6-Cl H CH₃ CH₃ H H n-C₄H₉1.121 6-Cl H CH₃ CH₃ H H 1-phenyl-1-cyclo- pentyl 1.122 6-Cl H CH₃ CH₃ HH 1-phenyl-1-cyclo- propyl 1.123 6-Cl H CH₃ CH₃ H H1-phenyl-1-cyclo-hexyl 1.124 6-Cl H CH₃ CH₃ H H C(CH₃)₂phenyl 1.125 6-ClH CH₃ CH₃ H H 2,6-dimethylphenyl 1.126 6-Cl H CH₃ CH₃ H H2,4,6-tri-isopropyl- phenyl 1.127 6-Cl H CH₃ CH₃ H H cyclohexyl 1.1286-Cl H CH₃ CH₃ H H benzyl 1.129 6-Cl H CH₃ CH₃ H H 1-adamantyl 1.1306-Cl H CH₃ CH₃ H H t-C₄H₉ 1.131 6-Cl H CH₃ CH₃ H H CH(phenyl)₂ 1.1326-Cl H CH₃ CH₃ H H cyclopropyl 1.133 6-Cl H CH₃ CH₃ H H CH(C₂H₅)₂ 1.1346-Cl H CH₃ CH₃ H H CH(n-C₃H₇)₂ 1.135 6-Cl H CH₃ CH₃ H H CH₂(cyclohexyl)1.136 6-Cl H CH₃ CH₃ H H CH₂CH₂(cyclo-hexyl) 1.137 6-Cl H CH₃ CH₃ H H3-(t-C₄H₉)cyclo-hex-1- yl 1.138 6-Cl H CH₃ CH₃ H H1-(4-chloro-phenyl)-1- cyclopentyl 1.139 6-Cl H CH₃ CH₃ H H1-(4-fluoro-phenyl)-1- cyclopentyl 1.140 6-Cl H CH₃ CH₃ H HCH₂C(CH₃)₂CH₃ 1.141 6-Cl H CH₃ CH₃ H H CH₂CH(phenyl)₂ 1.142 6-Cl H CH₃CH₃ H H 1-methyl-2,2-di-chloro- 1 -cyclopropyl 1.143 6-Cl H CH₃ CH₃ H H1-methyl-1-cyclohexyl 1.144 6-Cl H CH₃ CH₃ H H cyclopentyl 1.145 6-Cl HCH₃ CH₃ CH₃ CH₃ 4-Cl-phenyl 1.146 6-Cl H C₂H₅ C₂H₅ CH₃ CH₃ CH₃ 1.1476-Cl 5-Cl C₂H₅ C₂H₅ H H CH₃ 1.148 6-Cl H C₂H₅ C₂H₅ H H CH₃ 1.149 6-Cl HC₂H₅ C₂H₅ CH₃ C₂H₅ CH₃ 1.150 6-Cl H C₂H₅ C₂H₅ H H C₂H₅ 1.151 6-Cl H C₂H₅C₂H₅ H H i-C₃H₇ 1.152 6-Cl H C₂H₅ C₂H₅ H H n-C₃H₇ 1.153 6-Cl H C₂H₅ C₂H₅H H n-C₄H₉ 1.154 6-Cl H C₂H₅ C₂H₅ H H s-C₄H₉ 1.155 H 5-Cl C₂H₅ C₂H₅ H Ht-C₄H₉ 1.156 6-Cl H C₂H₅ C₂H₅ H H n-C₇H₁₅ 1.157 6-Cl H C₂H₅ C₂H₅ H Hn-C₁₁H₂₃ 1.158 6-Cl H C₂H₅ C₂H₅ H H n-C₁₃H₂₇ 1.159 6-Cl H C₂H₅ C₂H₅ H Hn-C₁₅H₃₁ 1.160 6-Cl H C₂H₅ C₂H₅ H H n-C₁₇H₃₅ 1.161 6-Cl 5-Cl C₂H₅ C₂H₅ HH n-C₁₁H₂₃ 1.162 6-Cl 5-F C₂H₅ C₂H₅ CH₃ CH₃ n-C₇H₁₅ 1.163 6-Cl H C₂H₅C₂H₅ H H phenyl 1.164 6-Cl H C₂H₅ C₂H₅ H H n-C₅H₁₁ 1.165 6-Cl H C₂H₅C₂H₅ H H biphenyl 1.166 6-Cl H C₂H₅ C₂H₅ H H phenoxyphenyl 1.167 6-Cl HC₂H₅ C₂H₅ H H 4-t-butyl-phenyl 1.168 6-Cl H C₂H₅ C₂H₅ H H2-chloro-phenyl 1.169 6-Cl H C₂H₅ C₂H₅ H H 2,6-difluoro-phenyl 1.1706-Cl H C₂H₅ C₂H₅ H H C(CH₃)₂C₃H_(7-n) 1.171 6-Cl H C₂H₅ C₂H₅ H HC(CH₃)₂C₃H_(7-n) 1.172 6-Cl H C₂H₅ C₂H₅ H H C(CH₃)₂C₂H₅ 1.173 6-Cl HC₂H₅ C₂H₅ H H n-C₆H₁₃ 1.174 6-Cl H C₂H₅ C₂H₅ H H n-C₁₀H₂₁ 1.175 6-Cl HC₂H₅ C₂H₅ H H CH(CH₃)C₃H₇n 1.176 6-Cl H C₂H₅ C₂H₅ H H n-C₅H₁₁ 1.177 6-ClH C₂H₅ C₂H₅ H H n-C₈H₁₇ 1.178 6-Cl H C₂H₅ C₂H₅ H H n-C₄H₉ 1.179 6-Cl HC₂H₅ C₂H₅ H H 1-phenyl-1-cyclo- pentyl 1.180 6-Cl H C₂H₅ C₂H₅ H H1-phenyl-1-cyclo- propyl 1.191 6-Cl H C₂H₅ C₂H₅ H H1-phenyl-1-cyclo-hexyl 1.192 6-Cl H C₂H₅ C₂H₅ H H C(CH₃)₂phenyl 1.1936-Cl H C₂H₅ C₂H₅ H H 2,6-dimethylphenyl 1.194 6-Cl H C₂H₅ C₂H₅ H H2,4,6-tri-isopropyl- phenyl 1.195 6-Cl H C₂H₅ C₂H₅ H H cyclohexyl 1.1966-Cl H C₂H₅ C₂H₅ H H benzyl 1.197 6-Cl H C₂H₅ C₂H₅ H H 1-adamantyl 1.1986-Cl H C₂H₅ C₂H₅ H H t-C₄H₉ 1.199 6-Cl H C₂H₅ C₂H₅ H H CH(phenyl)₂ 1.2006-Cl H C₂H₅ C₂H₅ H H cyclopropyl 1.201 6-Cl H C₂H₅ C₂H₅ H H CH(C₂H₅)₂1.202 6-Cl H C₂H₅ C₂H₅ H H CH(n-C₃H₇)₂ 1.203 6-Cl H C₂H₅ C₂H₅ H HCH₂(cyclohexyl) 1.204 6-Cl H C₂H₅ C₂H₅ H H CH₂CH₂(cyclo-hexyl) 1.2056-Cl H C₂H₅ C₂H₅ H H 3-(t-C₄H₉)cyclo-hex-1- yl 1.206 6-Cl H C₂H₅ C₂H₅ HH 1-(4-chloro-phenyl)-1- cyclopentyl 1.207 6-Cl H C₂H₅ C₂H₅ H H1-(4-fluoro-phenyl)-1- cyclopentyl 1.208 6-Cl H C₂H₅ C₂H₅ H HCH₂C(CH₃)₂CH₃ 1.209 6-Cl H C₂H₅ C₂H₅ H H CH₂CH(phenyl)₂ 1.210 6-Cl HC₂H₅ C₂H₅ H H 1-methyl-2,2-di-chloro- 1 -cyclopropyl 1.211 6-Cl H C₂H₅C₂H₅ H H 1-methyl-1-cyclohexyl 1.212 6-Cl H C₂H₅ C₂H₅ H H cyclopentyl1.213 6-Cl H C₂H₅ C₂H₅ CH₃ CH₃ 4-Cl-phenyl

TABLE 2 Compounds of formula (Xb)

No. L M T U R₂ R₂′ R 2.001 H Cl C₂H₅ CH₃ H H CH₃ 2.002 Cl Cl C₂H₅ CH₃ HH CH₃ 2.003 H F CH₃ CH₃ H H CH₃ 2.004 H Cl C₂H₅ CH₃ CH₃ H CH₃ 2.005 F ClC₂H₅ CH₃ H H C₂H₅ 2.006 H Cl C₂H₅ CH₃ H H i-C₃H₇ 2.007 H Cl C₂H₅ CH₃ H Hn-C₃H₇ 2.008 H Cl C₂H₅ CH₃ H H n-C₄H₉ 2.009 H Cl H CH₃ H H s-C₄H₉ 2.010H Cl C₂H₅ CH₃ H H t-C₄H₉ 2.011 H Cl C₂H₅ CH₃ H H n-C₇H₁₅ 2.012 H Cl C₂H₅CH₃ H H n-C₁₁H₂₃ 2.013 H Cl C₂H₅ CH₃ H H n-C₁₃H₂₇ 2.014 H Cl C₂H₅ CH₃ HH n-C₁₅H₃₁ 2.015 H Cl C₂H₅ CH₃ H H n-C₁₇H₃₅ 2.016 Cl Cl C₂H₅ CH₃ H Hn-C₁₁H₂₃ 2.017 Cl F CH₃ CH₃ H H n-C₇H₁₅ 2.018 H Cl C₂H₅ CH₃ H H phenyl2.019 H Cl C₂H₅ CH₃ H CH₃ phenyl 2.020 H Cl C₂H₅ CH₃ H H biphenyl 2.021H Cl C₂H₅ CH₃ H H phenoxyphenyl 2.022 H Cl C₂H₅ CH₃ H H 4-t-butyl-phenyl2.023 H Cl C₂H₅ CH₃ H H 2-chloro-phenyl 2.024 H Cl C₂H₅ CH₃ H H2,6-difluoro-phenyl 2.025 H H C₂H₅ H H H n-C₁₇H₃₅ 2.026 H H C₂H₅ C₂H₅CH₃ H n-C₇H₁₅ 2.027 H Cl C₂H₅ CH₃ C₂H₅ H CH₃ 2.028 H Cl C₂H₅ CH₃ n-C₃H₇H CH₃ 2.029 H Cl C₂H₅ CH₃ s-C₄H₉ H CH₃ 2.030 H Cl C₂H₅ CH₃ n-C₆H₁₃ H CH₃2.031 H Cl CH₃ CH₃ CH₃ H CH₃ 2.032 H F CH₃ CH₃ CH₃ H CH₃ 2.033 H Cl C₂H₅CH₃ H H cyclohexyl 2.034 H Cl C₂H₅ CH₃ H H vinyl 2.035 H Cl C₂H₅ CH₃ H Hallyl 2.036 H Cl C₂H₅ CH₃ H H 2-propargyl 2.037 H Cl C₂H₅ CH₃ H HC(CH₃)₂C₃H₇-n 2.038 H Cl C₂H₅ CH₃ H H O(CH₃)₂C₃H₇-n 2.039 H Cl C₂H₅ CH₃H H C(CH₃)₂C₂H₅ 2.040 H Cl C₂H₅ CH₃ H H n-C₆H₁₃ 2.041 H Cl C₂H₅ CH₃ H Hn-C₁₀H₂₁ 2.042 H Cl C₂H₅ CH₃ H H CH(CH₃)C₃H₇n 2.043 H Cl C₂H₅ CH₃ H Hn-C₅H₁₁ 2.044 H Cl C₂H₅ CH₃ H H n-C₈H₁₇ 2.045 H Cl C₂H₅ CH₃ H H n-C₄H₉2.046 H Cl C₂H₅ CH₃ H H 1-phenyl-1-cyclo-pentyl 2.047 H Cl C₂H₅ CH₃ H H1-phenyl-1-cyclo-propyl 2.048 H Cl C₂H₅ CH₃ H H 1-phenyl-1-cyclo-hexyl2.049 2.0H Cl C₂H₅ CH₃ H H C(CH₃)₂phenyl 2.050 H Cl C₂H₅ CH₃ H H2,6-dimethylphenyl 2.051 H Cl C₂H₅ CH₃ H H 2,4,6-tri-isopropyl-phenyl2.052 H Cl C₂H₅ CH₃ H H cyclohexyl 2.053 H Cl C₂H₅ CH₃ H H benzyl 2.054H Cl C₂H₅ CH₃ H H 1-adamantyl 2.055 H Cl C₂H₅ CH₃ H H t-C₄H₉ 2.056 H ClC₂H₅ CH₃ H H CH(phenyl)₂ 2.057 H Cl C₂H₅ CH₃ H H cyclopropyl 2.058 H ClC₂H₅ CH₃ H H CH(C₂H₅)₂ 2.059 H Cl C₂H₅ CH₃ H H CH(n-C₃H₇)₂ 2.060 H ClC₂H₅ CH₃ H H CH₂(cyclohexyl) 2.061 H Cl C₂H₅ CH₃ H H CH₂CH₂(cyclo-hexyl)2.062 H Cl C₂H₅ CH₃ H H 3-(t-C₄H₉)cyclo-hex-1-yl 2.063 H Cl C₂H₅ CH₃ H H1-(4-chloro-phenyl)-1- cyclopentyl 2.064 H Cl C₂H₅ CH₃ H H1-(4-fluoro-phenyl)-1- cyclopentyl 2.065 H Cl C₂H₅ CH₃ H H CH₂C(CH₃)₂CH₃2.066 H Cl C₂H₅ CH₃ H H CH₂CH(phenyl)₂ 2.067 H Cl C₂H₅ CH₃ H H1-methyl-2,2-di-chloro-1- cyclopropyl 2.068 H Cl C₂H₅ CH₃ H H1-methyl-1-cyclohexyl 2.069 H Cl C₂H₅ CH₃ H H cyclopentyl 2.070 H ClC₂H₅ CH₃ CH₃ CH₃ 4-Cl-phenyl 2.071 6-Cl H CH₃ CH₃ CH₃ CH₃ CH₃ 2.073 6-Cl5-Cl CH₃ CH₃ H H CH₃ 2.074 6-Cl H CH₃ CH₃ H H CH₃ 2.075 6-Cl H CH₃ CH₃CH₃ H CH₃ 2.076 6-Cl H CH₃ CH₃ H H C₂H₅ 2.077 6-Cl H CH₃ CH₃ H H i-C₃H₇2.078 6-Cl H CH₃ CH₃ H H n-C₃H₇ 2.079 6-Cl H CH₃ CH₃ H H n-C₄H₉ 2.0806-Cl H CH₃ CH₃ H H s-C₄H₉ 2.081 H 5-Cl CH₃ CH₃ H H t-C₄H₉ 2.082 6-Cl HCH₃ CH₃ H H n-C₇H₁₅ 2.083 6-Cl H CH₃ CH₃ H H n-C₁₁H₂₃ 2.084 6-Cl H CH₃CH₃ H H n-C₁₃H₂₇ 2.085 6-Cl H CH₃ CH₃ H H n-C₁₅H₃₁ 2.086 6-Cl H CH₃ CH₃H H n-C₁₇H₃₅ 2.087 6-Cl 5-Cl CH₃ CH₃ H H n-C₁₁H₂₃ 2.088 6-Cl 5-F CH₃ CH₃CH₃ CH₃ n-C₇H₁₅ 2.089 6-Cl H CH₃ CH₃ H H phenyl 2.090 6-Cl H CH₃ CH₃ H Hn-C₅H₁₁ 2.091 6-Cl H CH₃ CH₃ H H biphenyl 2.092 6-Cl H CH₃ CH₃ H Hphenoxyphenyl 2.093 6-Cl H CH₃ CH₃ H H 4-t-butyl-phenyl 2.094 6-Cl H CH₃CH₃ H H 2-chloro-phenyl 2.095 6-Cl H CH₃ CH₃ H H 2,6-difluoro-phenyl2.096 6-Cl H CH₃ CH₃ H H C(CH₃)₂C₃H₇-n 2.097 6-Cl H CH₃ CH₃ H HC(CH₃)₂C₃H₇-n 2.098 6-Cl H CH₃ CH₃ H H C(CH₃)₂C₂H₅ 2.099 6-Cl H CH₃ CH₃H H n-C₆H₁₃ 2.100 6-Cl H CH₃ CH₃ H H n-C₁₀H₂₁ 2.101 6-Cl H CH₃ CH₃ H HCH(CH₃)C₃H₇n 2.102 6-Cl H CH₃ CH₃ H H n-C₅H₁₁ 2.103 6-Cl H CH₃ CH₃ H Hn-C₈H₁₇ 2.104 6-Cl H CH₃ CH₃ H H n-C₄H₉ 2.105 6-Cl H CH₃ CH₃ H H1-phenyl-1-cyclo-pentyl 2.106 6-Cl H CH₃ CH₃ H H 1-phenyl-1-cyclo-propyl2.107 6-Cl H CH₃ CH₃ H H 1-phenyl-1-cyclo-hexyl 2.108 6-Cl H CH₃ CH₃ H HC(CH₃)₂phenyl 2.109 6-Cl H CH₃ CH₃ H H 2,6-dimethylphenyl 2.110 6-Cl HCH₃ CH₃ H H 2,4,6-tri-isopropyl-phenyl 2.111 6-Cl H CH₃ CH₃ H Hcyclohexyl 2.112 6-Cl H CH₃ CH₃ H H benzyl 2.113 6-Cl H CH₃ CH₃ H H1-adamantyl 2.114 6-Cl H CH₃ CH₃ H H t-C₄H₉ 2.115 6-Cl H CH₃ CH₃ H HCH(phenyl)₂ 2.116 6-Cl H CH₃ CH₃ H H cyclopropyl 2.117 6-Cl H CH₃ CH₃ HH CH(C₂H₅)₂ 2.118 6-Cl H CH₃ CH₃ H H CH(n-C₃H₇)₂ 2.119 6-Cl H CH₃ CH₃ HH CH₂(cyclohexyl) 2.120 6-Cl H CH₃ CH₃ H H CH₂CH₂(cyclo-hexyl) 2.1216-Cl H CH₃ CH₃ H H 3-(t-C₄H₉)cyclo-hex-1-yl 2.122 6-Cl H CH₃ CH₃ H H1-(4-chloro-phenyl)-1- cyclopentyl 2.123 6-Cl H CH₃ CH₃ H H1-(4-fluoro-phenyl)-1- cyclopentyl 2.124 6-Cl H CH₃ CH₃ H HCH₂C(CH₃)₂CH₃ 2.125 6-Cl H CH₃ CH₃ H H CH₂CH(phenyl)₂ 2.126 6-Cl H CH₃CH₃ H H 1-methyl-2,2-di-chloro-1- cyclopropyl 2.127 6-Cl H CH₃ CH₃ H H1-methyl-1-cyclohexyl 2.128 6-Cl H CH₃ CH₃ H H cyclopentyl 2.129 6-Cl HCH₃ CH₃ CH₃ CH₃ 4-Cl-phenyl 2.130 6-Cl H C₂H₅ C₂H₅ CH₃ CH₃ CH₃ 2.1316-Cl 5-Cl C₂H₅ C₂H₅ H H CH₃ 2.132 6-Cl H C₂H₅ C₂H₅ H H CH₃ 2.133 6-Cl HC₂H₅ C₂H₅ CH₃ C₂H₅ CH₃ 2.134 6-Cl H C₂H₅ C₂H₅ H H C₂H₅ 2.135 6-Cl H C₂H₅C₂H₅ H H i-C₃H₇ 2.136 6-Cl H C₂H₅ C₂H₅ H H n-C₃H₇ 2.137 6-Cl H C₂H₅ C₂H₅H H n-C₄H₉ 2.138 6-Cl H C₂H₅ C₂H₅ H H s-C₄H₉ 2.139 H 5-Cl C₂H₅ C₂H₅ H Ht-C₄H₉ 2.140 6-Cl H C₂H₅ C₂H₅ H H n-C₇H₁₅ 2.141 6-Cl H C₂H₅ C₂H₅ H Hn-C₁₁H₂₃ 2.142 6-Cl H C₂H₅ C₂H₅ H H n-C₁₃H₂₇ 2.143 6-Cl H C₂H₅ C₂H₅ H Hn-C₁₅H₃₁ 2.144 6-Cl H C₂H₅ C₂H₅ H H n-C₁₇H₃₅ 2.145 6-Cl 5-Cl C₂H₅ C₂H₅ HH n-C₁₁H₂₃ 2.146 6-Cl 5-F C₂H₅ C₂H₅ CH₃ CH₃ n-C₇H₁₅ 2.147 6-Cl H C₂H₅C₂H₅ H H phenyl 2.148 6-Cl H C₂H₅ C₂H₅ H H n-C₅H₁₁ 2.149 6-Cl H C₂H₅C₂H₅ H H biphenyl 2.150 6-Cl H C₂H₅ C₂H₅ H H phenoxyphenyl 2.151 6-Cl HC₂H₅ C₂H₅ H H 4-t-butyl-phenyl 2.152 6-Cl H C₂H₅ C₂H₅ H H2-chloro-phenyl 2.153 6-Cl H C₂H₅ C₂H₅ H H 2,6-difluoro-phenyl 2.1546-Cl H C₂H₅ C₂H₅ H H C(CH₃)₂C₃H₇-n 2.155 6-Cl H C₂H₅ C₂H₅ H HC(CH₃)₂C₃H₇-n 2.156 6-Cl H C₂H₅ C₂H₅ H H C(CH₃)₂C₂H₅ 2.157 6-Cl H C₂H₅C₂H₅ H H n-C₆H₁₃ 2.158 6-Cl H C₂H₅ C₂H₅ H H n-C₁₀H₂₁ 2.159 6-Cl H C₂H₅C₂H₅ H H CH(CH₃)C₃H₇n 2.160 6-Cl H C₂H₅ C₂H₅ H H n-C₅H₁₁ 2.161 6-Cl HC₂H₅ C₂H₅ H H n-C₈H₁₇ 2.162 6-Cl H C₂H₅ C₂H₅ H H n-C₄H₉ 2.163 6-Cl HC₂H₅ C₂H₅ H H 1-phenyl-1-cyclo-pentyl 2.164 6-Cl H C₂H₅ C₂H₅ H H1-phenyl-1-cyclo-propyl 2.165 6-Cl H C₂H₅ C₂H₅ H H1-phenyl-1-cyclo-hexyl 2.166 6-Cl H C₂H₅ C₂H₅ H H C(CH₃)₂phenyl 2.1676-Cl H C₂H₅ C₂H₅ H H 2,6-dimethylphenyl 2.168 6-Cl H C₂H₅ C₂H₅ H H2,4,6-tri-isopropyl-phenyl 2.169 6-Cl H C₂H₅ C₂H₅ H H cyclohexyl 2.1706-Cl H C₂H₅ C₂H₅ H H benzyl 2.171 6-Cl H C₂H₅ C₂H₅ H H 1-adamantyl 2.1726-Cl H C₂H₅ C₂H₅ H H t-C₄H₉ 2.173 6-Cl H C₂H₅ C₂H₅ H H CH(phenyl)₂ 2.1746-Cl H C₂H₅ C₂H₅ H H cyclopropyl 2.175 6-Cl H C₂H₅ C₂H₅ H H CH(C₂H₅)₂2.176 6-Cl H C₂H₅ C₂H₅ H H CH(n-C₃H₇)₂ 2.177 6-Cl H C₂H₅ C₂H₅ H HCH₂(cyclohexyl) 2.178 6-Cl H C₂H₅ C₂H₅ H H CH₂CH₂(cyclo-hexyl) 2.1796-Cl H C₂H₅ C₂H₅ H H 3-(t-C₄H₉)cyclo-hex-1-yl 2.180 6-Cl H C₂H₅ C₂H₅ H H1-(4-chloro-phenyl)-1- cyclopentyl 2.181 6-Cl H C₂H₅ C₂H₅ H H1-(4-fluoro-phenyl)-1- cyclopentyl 2.182 6-Cl H C₂H₅ C₂H₅ H HCH₂C(CH₃)₂CH₃ 2.183 6-Cl H C₂H₅ C₂H₅ H H CH₂CH(phenyl)₂ 2.184 6-Cl HC₂H₅ C₂H₅ H H 1-methyl-2,2-di-chloro-1- cyclopropyl 2.185 6-Cl H C₂H₅C₂H₅ H H 1-methyl-1-cyclohexyl 2.186 6-Cl H C₂H₅ C₂H₅ H H cyclopentyl2.187 6-Cl H C₂H₅ C₂H₅ CH₃ CH₃ 4-Cl-phenyl

TABLE 3 Compounds of formula (XIa)

No. Hal Y X Q R₂ R₂′ R 3.001 Cl NO₂ CH H H H CH₃ 3.002 Cl NO₂ N H H HCH₃ 3.003 F NO₂ CH H H H CH₃ 3.004 Cl NO₂ CH 3-CH₃ H H CH₃ 3.005 Cl CNCH H H H CH₃ 3.006 Cl CN N H H H CH₃ 3.007 Cl NO₂ CH H H H C₂H₅ 3.008 ClNO₂ N H H H C₂H₅ 3.009 F NO₂ CH H H H C₂H₅ 3.010 Cl NO₂ CH 2-CH₃ H HC₂H₅ 3.011 Cl CN CH H H H C₂H₅ 3.012 Cl NO₂ CH H H H n-C₃H₇ 3.013 Cl NO₂N H H H n-C₄H₉ 3.014 F NO₂ CH H H H s-C₄H₉ 3.015 Cl NO₂ CH 3-CH₃ H Ht-C₄H₉ 3.016 Cl CN CH H H H n-C₇H₁₅ 3.017 Cl CN N H H H n-C₁₁H₂₃ 3.018Cl NO₂ CH H H H n-C₁₃H₂₇ 3.019 Cl NO₂ N H H H n-C₁₅H₃₁ 3.020 F NO₂ CH HH H n-C₁₇H₃₅ 3.021 Cl NO₂ CH 2-CH₃ H H n-C₁₁H₂₃ 3.022 Cl CN CH H H Hn-C₇H₁₅ 3.023 Cl NO₂ CH H H H phenyl 3.024 Cl NO₂ N H H CH₃ phenyl 3.025F NO₂ CH H H H biphenyl 3.026 Cl NO₂ CH 3-CH₃ H H phenoxyphenyl 3.027 ClCN CH H H H 4-t-butyl-phenyl 3.028 Cl CN N H H H 2-chloro-phenyl 3.029Cl NO₂ CH 3-C₂H₅ H H 2,6-difluoro-phenyl 3.030 Cl CN CH 2-CH₃ H Hn-C₁₇H₃₅ 3.031 Cl CN N 3-CH₃ CH₃ H n-C₇H₁₅ 3.032 Cl CN N H H Hcyclohexyl 3.033 Cl CN N H H H vinyl 3.034 Cl CN CH H H H allyl 3.035 ClCN N H H H 2-propargyl 3.036 Cl NO₂ N H H H cyclohexyl 3.037 Cl NO₂ N HH H vinyl 3.038 Cl NO₂ N H H H allyl 3.039 Cl NO₂ CH H H H 2-propargyl3.040 Cl CN CH H C₂H₅ H C₂H₅ 3.041 Br NO₂ CH H H H n-C₃H₇ 3.042 Cl NO₂ NH C₂H₅ CH₃ n-C₄H₉ 3.043 F NO₂ CH H C₂H₅ H s-C₄H₉ 3.044 Br NO₂ CH 3-CH₃C₂H₅ H t-C₄H₉ 3.045 Cl CN CH H C₂H₅ H n-C₇H₁₅ 3.046 Cl NO₂ CH H H HC(CH₃)₂C₃H₇-n 3.047 Cl CN CH H H H C(CH₃)₂C₃H₇-n 3.048 Cl NO₂ CH H H HC(CH₃)₂C₂H₅ 3.049 Cl NO₂ CH H H H n-C₆H₁₃ 3.050 Cl NO₂ CH H H H n-C₁₀H₂₁3.051 Cl CN C₂H₅ CH₃ H H CH(CH₃)C₃H₇n 3.052 Cl NO₂ C₂H₅ CH₃ H H n-C₅H₁₁3.053 Cl CN C₂H₅ CH₃ H H n-C₈H₁₇ 3.054 Cl NO₂ C₂H₅ CH₃ H H n-C₄H₉ 3.055Cl NO₂ C₂H₅ CH₃ H H 1-phenyl-1-cyclo-pentyl 3.056 Cl CN C₂H₅ CH₃ H H1-phenyl-1-cyclo-propyl 3.057 Cl NO₂ C₂H₅ CH₃ H H 1-phenyl-1-cyclo-hexyl3.058 Cl CN C₂H₅ CH₃ H H C(CH₃)₂phenyl 3.059 Cl NO₂ C₂H₅ CH₃ H H2,6-dimethylphenyl 3.060 Cl NO₂ C₂H₅ CH₃ H H 2,4,6-tri-isopropyl-phenyl3.061 Cl CN C₂H₅ CH₃ H H cyclohexyl 3.062 Cl NO₂ C₂H₅ CH₃ H H benzyl3.063 Cl CN C₂H₅ CH₃ H H 1-adamantyl 3.064 Cl NO₂ C₂H₅ CH₃ H H t-C₄H₉3.065 Cl NO₂ C₂H₅ CH₃ H H CH(phenyl)₂ 3.066 Cl CN C₂H₅ CH₃ H Hcyclopropyl 3.067 Cl NO₂ C₂H₅ CH₃ H H CH(C₂H₅)₂ 3.068 Cl CN C₂H₅ CH₃ H HCH(n-C₃H₇)₂ 3.069 Cl NO₂ C₂H₅ CH₃ H H CH₂(cyclohexyl) 3.070 Cl NO₂ C₂H₅CH₃ H H CH₂CH₂(cyclo-hexyl) 3.071 Cl CN C₂H₅ CH₃ H H3-(t-C₄H₉)cyclo-hex-1-yl 3.072 Cl NO₂ C₂H₅ CH₃ H H1-(4-chloro-phenyl)-1-cyclopentyl 3.073 Cl CN C₂H₅ CH₃ H H1-(4-fluoro-phenyl)-1-cyclopentyl 3.074 Cl NO₂ C₂H₅ CH₃ H HCH₂C(CH₃)₂CH₃ 3.075 Cl NO₂ C₂H₅ CH₃ H H CH₂CH(phenyl)₂ 3.076 Cl NO₂ C₂H₅CH₃ H H 1-methyl-2,2-di-chloro-1-cyclopropyl 3.077 Cl NO₂ C₂H₅ CH₃ H H1-methyl-1-cyclohexyl 3.078 Cl CN C₂H₅ CH₃ H H cyclopentyl 3.079 Cl NO₂C₂H₅ CH₃ CH₃ CH₃ 4-Cl-phenyl

TABLE 4 Compounds of formula (XIIa)

No. Hal Y X T—U R₂ R₂′ R 4.001 Cl NO₂ CH —(CH₂)₃— H H CH₃ 4.002 Cl NO₂ N—(CH₂)₃— H H CH₃ 4.003 F NO₂ CH —(CH₂)₃— H H CH₃ 4.004 F NO₂ N —(CH₂)₃—H H CH₃ 4.005 Cl CN CH —(CH₂)₃— H H CH₃ 4.006 Cl CN N —(CH₂)₃— H H CH₃4.007 Cl NO₂ CH —(CH₂)₃— H H C₂H₅ 4.008 Cl NO₂ N —(CH₂)₃— H H C₂H₅ 4.009F NO₂ CH —(CH₂)₃— H H C₂H₅ 4.010 Cl NO₂ CH —(CH₂)₃— CH₃ H C₂H₅ 4.011 ClCN CH —(CH₂)₃— H H C₂H₅ 4.012 Cl NO₂ CH —(CH₂)₃— H H n-C₃H₇ 4.013 Cl NO₂N —(CH₂)₃— H H n-C₄H₉ 4.014 F NO₂ CH —(CH₂)₃— H H s-C₄H₉ 4.015 Cl NO₂ CH—(CH₂)₃— H H t-C₄H₉ 4.016 Cl CN CH —(CH₂)₃— H H n-C₇H₁₅ 4.017 Cl CN N—(CH₂)₃— H H n-C₁₁H₂₃ 4.018 Cl NO₂ CH —(CH₂)₃— H H n-C₁₃H₂₇ 4.019 Cl NO₂N —(CH₂)₃— H H n-C₁₅H₃₁ 4.020 F NO₂ CH —(CH₂)₃— H H n-C₁₇H₃₅ 4.021 ClNO₂ CH —(CH₂)₃— CH₃ CH₃ n-C₁₁H₂₃ 4.022 Cl CN CH —(CH₂)₃— CH₃ H n-C₇H₁₅4.023 Cl NO₂ CH —(CH₂)₃— H H phenyl 4.024 Cl NO₂ N —(CH₂)₃— H CH₃ phenyl4.025 F CN CH —(CH₂)₃— H H biphenyl 4.026 Cl NO₂ CH —(CH₂)₃— H Hphenoxyphenyl 4.027 Cl CN CH —(CH₂)₃— H H 4-t-butyl-phenyl 4.028 Cl CN N—(CH₂)₃— H H 2-chloro-phenyl 4.029 Cl NO₂ CH —(CH₂)₃— H H2,6-difluoro-phenyl 4.030 Cl CN CH —(CH₂)₃— H H n-C_(l7)H₃₅ 4.031 Br CNN —(CH₂)₃— CH₃ H n-C₇H₁₅ 4.032 Cl CN N —(CH₂)₃— H H cyclohexyl 4.033 ClCN N —(CH₂)₃— H H vinyl 4.034 Cl CN CH —(CH₂)₃— H H allyl 4.035 Cl CN N—(CH₂)₃— H H 2-propargyl 4.036 Cl NO₂ N —(CH₂)₃— H H cyclohexyl 4.037 ClNO₂ N —(CH₂)₃— H H vinyl 4.038 Cl NO₂ N —(CH₂)₃— H H allyl 4.039 Cl NO₂CH —CH₂OCH₂— H H 2-propargyl 4.040 Cl NO₂ CH —CH₂OCH₂— H H CH₃ 4.041 ClNO₂ N —CH₂OCH₂— H H CH₃ 4.042 F NO₂ CH —CH₂OCH₂— H H CH₃ 4.043 F NO₂ N—CH₂OCH₂— H H CH₃ 4.044 Cl CN CH —CH₂OCH₂— H H CH₃ 4.045 Cl CN N—CH₂OCH₂— H H CH₃ 4.045 Cl NO₂ CH —CH₂OCH₂— H H C₂H₅ 4.047 Cl NO₂ N—CH₂OCH₂— H H C₂H₅ 4.048 F NO₂ CH —CH₂OCH₂— H H C₂H₅ 4.049 Cl NO₂ CH—CH₂OCH₂— CH₃ H C₂H₅ 4.050 Cl CN CH —CH₂OCH₂— H H C₂H₅ 4.051 Cl NO₂ CH—CH₂OCH₂— H H n-C₃H₇ 4.052 Cl NO₂ N —CH₂OCH₂— H H n-C₄H₉ 4.053 F NO₂ CH—CH₂OCH₂— H H s-C₄H₉ 4.054 Cl NO₂ CH —CH₂OCH₂— H H t-C₄H₉ 4.055 Cl CN CH—CH₂OCH₂— H H n-C₇H₁₅ 4.056 Cl CN N —CH₂OCH₂— H H n-C₁₁H₂₃ 4.057 Cl NO₂CH —CH₂OCH₂— H H n-C₁₃H₂₇ 4.058 Cl NO₂ N —CH₂OCH₂— H H n-C₁₅H₃₁ 4.059 FNO₂ CH —CH₂OCH₂— H H n-C₁₇H₃₅ 4.060 Cl NO₂ CH —CH₂OCH₂— CH₃ CH₃ n-C₁₁H₂₃4.061 Cl CN CH —CH₂OCH₂— CH₃ H n-C₇H₁₅ 4.062 Cl NO₂ CH —CH₂OCH₂— H Hphenyl 4.063 Cl NO₂ N —CH₂OCH₂— H CH₃ phenyl 4.064 F CN CH —CH₂OCH₂— H Hbiphenyl 4.065 Cl NO₂ CH —CH₂OCH₂— H H phenoxyphenyl 4.066 Cl CN CH—CH₂OCH₂— H H 4-t-butyl-phenyl 4.067 Cl CN N —CH₂OCH₂— H H2-chloro-phenyl 4.068 Cl NO₂ CH —CH₂OCH₂— H H 2,6-difluoro-phenyl 4.069Cl CN CH —CH₂OCH₂— H H n-C₁₇H₃₅ 4.070 Br CN N —CH₂OCH₂— CH₃ H n-C₇H₁₅4.071 Cl CN N —CH₂OCH₂— H H cyclohexyl 4.072 Cl CN N —CH₂OCH₂— H H vinyl4.073 Cl CN CH —CH₂OCH₂— H H allyl 4.074 Cl CN N —CH₂OCH₂— H H2-propargyl 4.075 Cl NO₂ N —CH₂OCH₂— H H cyclohexyl 4.076 Cl NO₂ N—CH₂OCH₂— H H vinyl 4.077 Cl NO₂ N —CH₂OCH₂— H H allyl 4.078 Cl NO₂ CH—CH₂OCH₂— H H 2-propargyl 4.079 Cl NO₂ CH —CH₂N(CH₃)CH₂— H H CH₃ 4.080Cl NO₂ N —CH₂N(CH₃)CH₂— H H CH₃ 4.081 F NO₂ CH —CH₂N(CH₃)CH₂— H H CH₃4.082 F NO₂ N —CH₂N(CH₃)CH₂— H H CH₃ 4.083 Cl CN CH —CH₂N(CH₃)CH₂— H HCH₃ 4.084 Cl CN N —CH₂N(CH₃)CH₂— H H CH₃ 4.085 Cl NO₂ CH —CH₂N(CH₃)CH₂—H H C₂H₅ 4.086 Cl NO₂ N —CH₂N(CH₃)CH₂— H H C₂H₅ 4.087 F NO₂ CH—CH₂N(CH₃)CH₂— H H C₂H₅ 4.088 Cl NO₂ CH —CH₂N(CH₃)CH₂— CH₃ H C₂H₅ 4.089Cl CN CH —CH₂N(CH₃)CH₂— H H C₂H₅ 4.090 Cl NO₂ CH —CH₂N(CH₃)CH₂— H Hn-C₃H₇ 4.091 Cl NO₂ N —CH₂N(CH₃)CH₂— H H n-C₄H₉ 4.092 F NO₂ CH—CH₂N(CH₃)CH₂— H H s-C₄H₉ 4.093 Cl NO₂ CH —CH₂N(CH₃)CH₂— H H t-C₄H₉4.094 Cl CN CH —CH₂N(CH₃)CH₂— H H n-C₇H₁₅ 4.095 Cl CN N —CH₂N(CH₃)CH₂— HH n-C₁₁H₂₃ 4.096 Cl NO₂ N —(CH₂)₃— H H CH(CH₃)C₃H₇-n 4.097 Cl CN N—(CH₂)₃— H H C(CH₃)₂C₃H₇-n 4.098 Cl NO₂ N —(CH₂)₃— H H C(CH₃)₂C₂H₅ 4.099Cl NO₂ N —(CH₂)₃— H H n-C₆H₁₃ 4.100 Cl NO₂ N —(CH₂)₃— H H n-C₁₀H₂₁ 4.101Cl CN C₂H₅ CH₃ H H CH(CH₃)C₃H₇n 4.102 Cl NO₂ C₂H₅ CH₃ H H n-C₅H₁₁ 4.103Cl NO₂ C₂H₅ CH₃ H H n-C₈H₁₇ 4.104 F NO₂ C₂H₅ CH₃ H H n-C₄H₉ 4.105 Cl NO₂C₂H₅ CH₃ H H 1-phenyl-1-cyclo-pentyl 4.106 Cl CN C₂H₅ CH₃ H H1-phenyl-1-cyclo-propyl 4.107 Cl CN C₂H₅ CH₃ H H 1-phenyl-1-cyclo-hexyl4.108 Cl NO₂ C₂H₅ CH₃ H H C(CH₃)₂phenyl 4.109 Cl CN C₂H₅ CH₃ H H2,6-dimethylphenyl 4.110 Cl NO₂ C₂H₅ CH₃ H H 2,4,6-tri-isopropyl-phenyl4.111 Cl NO₂ C₂H₅ CH₃ H H cyclohexyl 4.112 Cl NO₂ C₂H₅ CH₃ H H benzyl4.113 Cl CN C₂H₅ CH₃ H H 1-adamantyl 4.114 Cl NO₂ C₂H₅ CH₃ H H t-C₄H₉4.115 Cl NO₂ C₂H₅ CH₃ H H CH(phenyl)₂ 4.116 F NO₂ C₂H₅ CH₃ H Hcyclopropyl 4.117 Cl NO₂ C₂H₅ CH₃ H H CH(C₂H₅)₂ 4.118 Cl CN C₂H₅ CH₃ H HCH(n-C₃H₇)₂ 4.119 Cl CN C₂H₅ CH₃ H H CH₂(cyclohexyl) 4.120 Cl NO₂ C₂H₅CH₃ H H CH₂CH₂(cyclo-hexyl) 4.121 Cl CN C₂H₅ CH₃ H H3-(t-C₄H₉)cyclo-hex-1-yl 4.122 Cl NO₂ C₂H₅ CH₃ H H1-(4-chloro-phenyl)-1- cyclopentyl 4.123 Cl NO₂ C₂H₅ CH₃ H H1-(4-chloro-phenyl)-1- cyclopentyl 4.124 Cl NO₂ C₂H₅ CH₃ H HCH₂C(CH₃)₂CH₃ 4.125 Cl NO₂ C₂H₅ CH₃ H H CH₂CH(phenyl)₂ 4.126 Cl CN C₂H₅CH₃ H H 1-methyl-2,2-di-chloro-1- cyclopropyl 4.127 Cl NO₂ C₂H₅ CH₃ H H1-methyl-1-cyclohexyl 4.128 Cl NO₂ C₂H₅ CH₃ H H cyclopentyl 4.129 Cl NO₂C₂H₅ CH₃ CH₃ CH₃ 4-Cl-phenyl

Further typical and interesting compounds of formula (I) are:

TABLE 5 Compounds of formula (XXa)

No. M L T U R₂ R₂′ Hal Physical Data 5.001 6-Cl H C₂H₅ CH₃ H H F 5.0026-Cl 5-Cl C₂H₅ CH₃ H H F 5.003 6-Cl H CH₃ CH₃ H H F 5.004 6-Cl H C₂H₅CH₃ CH₃ H F 5.005 6-Cl H C₂H₅ CH₃ H H Cl m.p. 142-143° C. 5.006 6-Cl HC₂H₅ CH₃ H H Br 5.007 6-Cl H C₂H₅ CH₃ H H I 5.008 6-Cl H C₂H₅ CH₃ CH₃ HCl 5.009 6-Cl H H CH₃ CH₃ H Br 5.010 H 5-Cl C₂H₅ CH₃ H H Cl 5.011 6-Cl HC₂H₅ CH₃ H H Cl 5.012 6-Cl H C₂H₅ H H H Br 5.013 6-Cl H C₂H₅ C₂H₅ CH₃ HBr 5.014 6-Cl H C₂H₅ CH₃ C₂H₅ H F 5.015 6-Cl H C₂H₅ CH₃ n-C₃H₇ H F 5.0166-Cl H C₂H₅ CH₃ s-C₄H₉ H F 5.017 6-Cl H C₂H₅ CH₃ n-C₆H₁₃ H F 5.018 6-ClH CH₃ CH₃ CH₃ H F 5.019 6-Cl 4-F CH₃ CH₃ CH₃ H F 5.020 6-Cl H C₂H₅ CH₃CH₃ CH₃ I 5.021 6-Cl H C₂H₅ CH₃ CH₃ CH₃ F 5.022 6-Cl H C₂H₅ CH₃ C₂H₅ CH₃Cl 5.023 6-Cl H C₂H₅ CH₃ CH₃ CH₃ Br 5.024 6-Cl H C₂H₅ CH₃ C₂H₅ C₂H₅ I5.025 6-Cl H C₂H₅ CH₃ n-C₃H₇ C₂H₅ Cl 5.026 6-Cl H C₂H₅ CH₃ CH₃ s-C₄H₉ Br5.027 6-Cl H C₂H₅ CH₃ CH₃ n-C₃H₇ I 5.028 6-Cl H C₂H₅ CH₃ s-C₄H₉ C₂H₅ F5.029 6-Cl H C₂H₅ CH₃ s-C₄H₉ n-C₃H₇ Cl 5.030 6-Cl H C₂H₅ C₂H₅ CH₃ n-C₃H₇I 5.031 6-Cl H C₂H₅ CH₃ C₂H₅ CH₃ F 5.032 6-Cl H C₂H₅ CH₃ n-C₃H₇ CH₃ F5.033 6-Cl H C₂H₅ CH₃ s-C₄H₉ CH₃ F 5.034 6-Cl H C₂H₅ CH₃ n-C₆H₁₃ H F

TABLE 6 Compounds of formula (XXb)

No. L M T U R₂ R₂′ Hal 6.001 H Cl C₂H₅ CH₃ H H Cl 6.002 Cl Cl C₂H₅ CH₃ HH Cl 6.003 H F CH₃ CH₃ H H Cl 6.004 H Cl C₂H₅ CH₃ CH₃ H Cl 6.005 F ClC₂H₅ CH₃ H H F 6.006 H Cl C₂H₅ CH₃ H H F 6.007 H Cl C₂H₅ CH₃ H H Br6.008 H Cl C₂H₅ CH₃ CH₃ H F 6.009 H Cl H CH₃ H H Cl 6.010 H Cl C₂H₅ C₂H₅H H Cl 6.011 H Cl C₂H₅ CH₃ H H I 6.012 H Cl C₂H₅ CH₃ CH₃ H I 6.013 H ClC₂H₅ CH₃ CH₃ CH₃ I 6.014 H H C₂H₅ C₂H₅ CH₃ H F 6.015 H Cl C₂H₅ CH₃ C₂H₅H Cl 6.016 H Cl C₂H₅ CH₃ n-C₃H₇ H Cl 6.017 H Cl C₂H₅ CH₃ s-C₄H₉ H Cl6.018 H Cl C₂H₅ CH₃ n-C₆H₁₃ H Cl 6.019 H Cl CH₃ CH₃ CH₃ H Cl 6.020 H FCH₃ CH₃ CH₃ H Cl 6.021 H Cl C₂H₅ CH₃ C₂H₅ CH₃ I 6.022 H Cl C₂H₅ CH₃ CH₃H Br 6.023 H Cl C₂H₅ CH₃ CH₃ CH₃ F

TABLE 7 Compounds of formula (XXc)

No. Hal Y X Q R₂ R₂′ Hal′ 7.001 Cl NO₂ CH H H H Cl 7.002 Cl NO₂ N H H HCl 7.003 F NO₂ CH H H H Cl 7.004 Cl NO₂ CH 3-CH₃ H H Cl 7.005 Cl CN CH HH H Cl 7.006 Cl CN N H H H Cl 7.007 Cl NO₂ CH H H H F 7.008 Cl NO₂ N H HH F 7.009 F NO₂ CH H H H F 7.010 Cl NO₂ CH 2-CH₃ H H F 7.011 Cl CN CH HH H Br 7.012 Cl NO₂ CH H H H Br 7.013 Cl NO₂ N H H H I 7.014 F NO₂ CH HH H I 7.015 Cl NO₂ CH 3-CH₃ H H Cl 7.016 Cl CN CH H CH₃ H Cl 7.017 Cl CNN H CH₃ H Cl 7.018 Cl NO₂ CH H CH₃ H Cl 7.019 Cl NO₂ N H CH₃ H Cl 7.020F NO₂ CH H CH₃ H Cl 7.021 Cl NO₂ CH 2-CH₃ CH₃ H Cl 7.022 Cl CN CH H CH₃H F 7.023 Cl NO₂ CH H CH₃ H F 7.024 Cl NO₂ N H CH₃ CH₃ F 7.025 F NO₂ CHH CH₃ H F 7.026 Cl NO₂ CH 3-CH₃ CH₃ H F 7.027 Cl CN CH H CH₃ H Br 7.028Cl CN N H CH₃ H Br 7.029 Cl NO₂ CH 3-C₂H₅ H H Cl 7.030 Cl CN CH 2-CH₃CH₃ CH₃ Cl

TABLE 8 Compounds of formula (XXd)

No. Hal Y X T—U R₂ R′₂ Hal′ 8.001 Cl NO₂ CH —(CH₂)₃— H H Cl 8.002 Cl NO₂N —(CH₂)₃— H H Cl 8.003 F NO₂ CH —(CH₂)₃— H H Cl 8.004 F NO₂ N —(CH₂)₃—H H Cl 8.005 Cl CN CH —(CH₂)₃— H H Cl 8.006 Cl CN N —(CH₂)₃— H H Cl8.007 Cl NO₂ CH —(CH₂)₃— H H F 8.008 Cl NO₂ N —(CH₂)₃— H H F 8.009 F NO₂CH —(CH₂)₃— H H F 8.010 Cl NO₂ CH —(CH₂)₃— CH₃ H F 8.011 Cl CN CH—(CH₂)₃— H H Br 8.012 Cl NO₂ CH —(CH₂)₃— H H Br 8.013 Cl NO₂ N —(CH₂)₃—H H I 8.014 F NO₂ CH —(CH₂)₃— H H I 8.015 Cl NO₂ CH —(CH₂)₃— CH₃ H Cl8.016 Cl CN CH —(CH₂)₃— CH₃ H Cl 8.017 Cl CN N —(CH₂)₃— CH₃ H Cl 8.018Cl NO₂ CH —(CH₂)₃— CH₃ H Cl 8.019 Cl NO₂ N —(CH₂)₃— CH₃ CH₃ Cl 8.020 FNO₂ CH —(CH₂)₃— CH₃ CH₃ Cl 8.021 Cl NO₂ CH —(CH₂)₃— CH₃ CH₃ Cl 8.022 ClCN CH —(CH₂)₃— CH₃ H F 8.023 Cl NO₂ CH —(CH₂)₃— H H F 8.024 Cl NO₂ N—(CH₂)₃— H CH₃ F 8.025 F CN CH —(CH₂)₂— CH₃ CH₃ F 8.026 Cl NO₂ CH—(CH₂)₂— CH₃ CH₃ F 8.027 Cl CN CH —(CH₂)₃— H H Br 8.028 Cl CN N —(CH₂)₃—H H Br 8.029 Cl NO₂ CH —(CH₂)₃— C₂H₅ H Cl 8.030 Cl CN CH —(CH₂)₃— C₂H₅ HCl

It has now been found that systemic administration, for example by oral,percutaneous administration, or preferably topical application, forexample in pour-on, spot-on or spray form, of a compound of formula (I)in an amount effective against insects is able drastically to reduce orcompletely to prevent attack by parasites on warm-blooded animals over aprolonged period.

The present invention therefore relates to the long-term control ofparasites, especially blood-sucking insects but more especially thelong-term control of fleas.

The compounds of formula (I) are distinguished inter alia by excellentactivity against fleas, not only adult fleas being rapidly killed butalso, by a circuitous route, the juvenile stages of the fleas. Flealarvae hatching out from the flea eggs feed mainly on the excreta of theadult fleas. Since the compounds of formula (I) according to theinvention kill the adult fleas very rapidly, the necessary excreta areabsent and the juvenile stages are deprived of the nutrient medium, sothat they perish before reaching the adult stage.

The present invention therefore relates preferably to a method ofcontrolling parasites on human beings, domestic animals, productivelivestock and pets, which comprises administering systemically orpreferably topically to the warm-blooded animal an effective amount of acomposition comprising at least one compound of formula (I) or aphysiologically tolerable salt thereof.

Long-term action is achieved by the compounds of formula (I) accordingto the invention using various forms of administration, for example byadministering the active ingredient to the animal to be treatedexternally or internally in a formulated form. “Formulated” in this casemeans, e.g., in the form of a powder, a tablet or granules, in liposomesor a capsule, in the form of an emulsion, a foam or a spray, inmicroencapsulated form or in pour-on or spot-on form. It will beunderstood that all orally administrable compositions may comprise, inaddition to customary formulation substances, further additives thatencourage the host animal to take the composition orally voluntarily,e.g., suitable odoronts and flavorings.

Percutaneous administration, for example by subcutaneous orintramuscular injection or as a depot preparation in the form of animplant, and topical application, e.g., in pour-on or spot-on form,represent preferred subjects of this invention on account of their beingeasy to carry out. A further mode of administration is oraladministration, e.g., in the form of a tablet. Percutaneous and topicalforms of administration are of particular interest and give excellentresults.

Percutaneous forms of administration include, e.g., subcutaneous,intramuscular and even intravenous administration of injectable forms.In addition to the customary syringes with needles, it is also possibleto use needle-less high-pressure syringe devices.

Pour-on and spot-on formulations are especially preferred as topicalforms of administration, but administration in the form of sprays,ointments, solutions or powders may also be expedient.

By selection of a suitable formulation it is possible to enhance theability of the active ingredients to penetrate into the living tissue ofthe host animal and/or to maintain its availability. That is importantwhen, for example, rather sparingly soluble active ingredients are used,the low solubility of which requires means for enhancing solubility,since in such cases the animal's body fluid will be capable ofdissolving only small amounts of active ingredient at a time.

In order to obtain a greatly delayed release of active ingredient, acompound of formula (I) according to the invention may also be presentin a matrix formulation which physically prevents the active ingredientfrom being released and excreted prematurely and maintains thebioavailability of the active ingredient. Such a matrix formulation isinjected into the body, e.g., intramuscularly or subcutaneously, andremains there as a form of depot from which active ingredient isreleased continuously. Such matrix formulations are known to a personskilled in the art. They are generally wax-like, semi-solid substances,e.g., vegetable waxes and polyethylene glycols having a high molecularweight, or solid polymer formulations, e.g., so-called microspheres.

The rate of release of the active ingredient from the implant and thusthe period of time over which the implant exhibits an action isgenerally determined by the accuracy with which the implant has beencalibrated (amount of active ingredient in the implant), the environmentaround the implant and the polymer formulation from which the implanthas been made.

The administration of veterinary medicinal additives to animal food iswell-known in the field of animal health. It is usual first to prepare aso-called premix in which the active ingredient is dispersed in a liquidor is present in finely divided form in solid carriers. The premix cannormally comprise about 1-800 mg of compound per kg of premix, dependingon the desired final concentration in the food.

Since the compounds of formula (I) according to the invention may behydrolysed by the constituents of the food, they should be formulated ina protective matrix, e.g., in gelatin, before being added to the premix.

The present invention accordingly relates also to the aspect ofcontrolling parasites by administering to the host animal with its fooda compound of formula (I) that has been protected against hydrolysis.

A compound of formula (I) according to the invention is advantageouslyadministered in a dose of from 0.01-800 mg/kg, preferably from 0.1-200mg/kg, especially from 0.5-30 mg/kg body weight, based on the hostanimal.

A good dose that can be administered regularly to the host animal isfrom 0.5-100 mg/kg, preferably from 0.1-40 mg/kg body weight. Theadministration is effected at suitable intervals in dependence upon themode of administration and body weight.

The total dose may vary for the same active ingredient from one speciesof animal to another and also within a species of animal, since itdepends inter alia on the weight, age and constitution of the hostanimal.

When used according to the invention, the compound of formula (I)according to the invention will normally be administered not in pureform but preferably in the form of a composition that comprises, inaddition to the active ingredient, constituents that assistadministration, suitable constituents being those which are tolerated bythe host animal. It is of course possible, as well as controlling theadult parasites in accordance with the invention, additionally to useconventional methods to control the juvenile stages of the fleas,although the latter is not absolutely essential.

Such compositions to be administered in accordance with the inventiongenerally comprise from 0.1-99% by weight, especially from 0.1-95% byweight, of a compound of formula (I) according to the invention and from99.9-1% by weight, especially from 99.9-5% by weight, of a solid orliquid, physiologically tolerable carrier, including from 0-25% byweight, especially from 0.1-25% by weight, of a non-toxic dispersant.

Whereas commercial products will preferably be formulated asconcentrates, the end user will normally employ dilute formulations.

Such formulations may also comprise further ingredients, such asstabilisers, antifoams, viscosity regulators, binders and tackifiers, aswell as other active ingredients for obtaining special effects.

The physiologically tolerable carriers known from veterinary medicinalpractice for oral, percutaneous and topical administration can be usedas formulation adjuvants. Some examples are given below.

Suitable carriers are especially fillers, such as sugars, e.g., lactose,saccharose, mannitol or sorbitol, cellulose preparations and/or calciumphosphates, e.g., tricalcium phosphate or calcium hydrogen phosphate;and binders, such as starch pastes using, e.g., maize, wheat, rice orpotato starch, gelatin, tragacanth, methylcellulose and/or, if desired,disintegrators, such as the above-mentioned starches, also carboxymethylstarch, cross-linked polyvinylpyrrolidone, agar, alginic acid or a saltthereof, such as sodium alginate. Adjuvants are especially flowconditioners and lubricants, e.g., silicic acid, talc, stearic acid orsalts thereof, such as magnesium or calcium stearate, and/orpolyethylene glycol. Dragée cores can be provided with suitable,optionally enteric, coatings, there being used inter alia concentratedsugar solutions which may comprise gum arabic, talc,polyvinylpyrrolidone, polyethylene glycol and/or titanium dioxide, orcoating solutions in suitable organic solvents or solvent mixtures, or,for the preparation of enteric coatings, solutions of suitable cellulosepreparations, such as acetylcellulose phthalate orhydroxypropylmethylcellulose phthalate. Dyes, flavorings or pigments maybe added to the tablets or dragee coatings, e.g., for identificationpurposes or to indicate different doses of active ingredient.

Other orally administrable compositions are hard gelatin capsules, andalso soft-sealed capsules made of gelatin and a plasticiser, such asglycerol or sorbitol. The hard gelatin capsules may comprise the activeingredient in the form of granules, e.g., in admixture with fillers,such as lactose, binders, such as starches, and/or glidants, such astalc or magnesium stearate, and, optionally, stabilizers. In softcapsules, the active ingredient is preferably dissolved or suspended insuitable liquids, such as fatty oils, paraffin oil or liquidpolyethylene glycols, to which stabilizers may also have been added.Preference is given inter alia to capsules that may easily be bittenthrough or swallowed without being chewed.

The pour-on or spot-on method comprises applying the compound of formula(I) to a locally limited area of the skin or coat, advantageously on theback of the neck or the backbone of the animal. This is carried out, forexample, by applying the pour-on or spot-on formulation using a swab orspray to a relatively small area of the coat from where the activeingredient becomes distributed over a wide area of the coat almostautomatically as a result of the spreading constituents of theformulation assisted by the movements of the animal.

Pour-on and spot-on formulations advantageously comprise carriers thatassist rapid distribution over the surface of the skin and in the coatof the host animal and are generally termed spreading oils. There aresuitable, e.g., oily solutions; alcoholic and isopropanolic solutions,e.g., solutions of 2-octyl dodecanol or oleyl alcohol; solutions inesters of monocarboxylic acids, such as isopropyl myristate, isopropylpalmitate, lauric acid oxalic ester, oleic acid oleyl ester, oleic aciddecyl ester, hexyl laurate, oleyl oleate, decyl oleate, caproic acidesters of saturated fatty alcohols of chain length C₁₂-C₁₈; solutions ofesters of dicarboxylic acids, such as dibutyl phthalate, diisopropylisophthalate, adipic acid diisopropyl ester, di-n-butyl adipate orsolutions of esters of aliphatic acids, e.g., glycols. It may beadvantageous for a dispersant known from the pharmaceutical or cosmeticindustry also to be present. Examples are pyrrolidin-2-one,N-alkylpyrrolidin-2-one, acetone, polyethylene glycol and its ethers andesters, propylene glycol or synthetic triglycerides.

The oily solutions include, e.g., vegetable oils, such as olive oil,groundnut oil, sesame oil, pine oil, linseed oil and castor oil. Thevegetable oils may also be in epoxidised form. It is also possible touse paraffins and silicone oils.

Generally a pour-on or spot-on formulation will contain from 1-20% byweight of a compound of formula (I), from 0.1-50% by weight dispersantand from 45-98.9% by weight solvent.

The pour-on and spot-on methods can be used especially advantageouslyfor herd animals, such as cattle, horses, sheep and pigs, where it isdifficult or time-consuming to treat all the animals orally or viainjection. By virtue of its simplicity, this method can of course alsobe used for all other animals, including individual domestic animals andpets, and is welcomed especially by the keepers of the animals becauseit can frequently be carried out without the expert assistance of aveterinary surgeon.

Suitable for parenteral and percutaneous administration are oilyinjection solutions or suspensions, there being used suitable lipophilicsolvents or vehicles, such as fatty oils, for example sesame oil, orsynthetic fatty acid esters, e.g., ethyl oleate, or triglycerides, oraqueous injection solutions or suspensions that, compriseviscosity-increasing substances, e.g., sodium carboxymethylcellulose,sorbitol and/or dextran, and, optionally, stabilizers.

The compositions of the present invention can be prepared in a mannerknown per se, e.g., by means of conventional mixing, granulating,confectioning, dissolving or lyophilizing processes. For example,pharmaceutical compositions for oral administration can be obtained bycombining the active ingredient with solid carriers, optionallygranulating a resulting mixture, and processing the mixture or granules,if desired or necessary, after the addition of suitable excipients, toform tablets or dragee cores.

The following Examples and patent claims illustrate the inventiondescribed above, but do not limit its scope in any way. Temperatures aregiven in degrees Celsius. In the following Formulation Examples theexpression “compound of formula (I)” is used to represent a compound ofTables 1-3, especially benzoic acid({1-[(6-chloro-pyridin-3-ylmethyl)-ethyl-amino]-2-nitro-vinyl}-methyl-carbamoyloxy)-methylester.

FORMULATION EXAMPLES Example 1 Tablets Comprising 25 mg of a Compound ofFormula (I) Can be Prepared as Follows:

Constituents (for 1000 tablets) compound of formula (I)  25.0 g lactose100.7 g wheat starch  7.5 g polyethylene glycol 6000  5.0 g talcum  5.0g magnesium stearate  1.8 g demineralized water q.s.

Preparation: All the solid ingredients are first forced through a sieveof 0.6 mM mesh size. Then the active ingredient, the lactose, the talcumand half the starch are mixed together. The other half of the starch issuspended in 40 mL of water and the suspension is added to a boilingsolution of the polyethylene glycol in 100 mL of water. The resultingstarch paste is added to the main batch and the mixture is granulated,if necessary with the addition of water. The granules are driedovernight at 35° C., forced through a sieve of 1.2 mM mesh size, mixedwith the magnesium stearate and compressed to form tablets which have amesh size of about 6 mM and which are concave on both sides.

Example 2 Injection Solution

compound of formula (I) 0.1-10%, preferably 0.5-5% non-ionic surfactant0.1-30%, preferably 0.5-10% mixture of ethanol and propylene glycol 60-99%, preferably 85-90%

Example 3 Injection Suspension (Aqueous or Oily)

compound of formula (I) 0.1-20%, preferably 1-10% non-ionic surfactant0.1-20%, preferably 1-10% water or vegetable oil  60-99%, preferably85-95%

Example 4 Oily Injectable

Oily vehicle (slow release) A. compound of formula (I) 0.1-1.0 ggroundnut oil ad 100 mL or B. compound of formula (I) 0.1-1.0 g sesameoil ad 100 mL

Preparation: The active ingredient is dissolved in a portion of the oil,with stirring and optionally with gentle heating, and after cooling thesolution is made up to the desired volume and sterile-filtered through asuitable 0.22 mM membrane filter.

Example 5 Pour-On

A. compound of formula (I) 10% epoxidized soybean oil  5% oleyl alcohol85% B. compound of formula (I) 20% pyrrolidin-2-one 15% isopropylmyristate 65%

It is also possible to add to the described compositions biologicallyactive substances or additives that have neutral behaviour towards thecompounds of formula (I) and have no adverse effect on the host animalto be treated, and also mineral salts or vitamins.

Analogously to the described formulations of Examples 1-8 it is alsopossible to prepare further preparations having active ingredients offormula (I).

Example 6 Control of Adult Fleas in Cats by Means of Pour-On Application

Test Protocol for Each Test Compound:

In order to determine the effectiveness of the test compounds againstfully grown fleas, four groups each of two cats are used. Each cat isinfested with 100 cat fleas [Ctenocephalides felis (Bouche)] and treatedwith 20 mg of active ingredient per kg body weight. The treatment iseffected by applying the formulation to a locally limited area on theback of the cat's neck. While one group is infested with fleas but istreated only with a placebo, that is to say a formulation without activeingredient, and serves as control, another group is treated withnitenpyram as comparison substance; the two remaining groups receive thetest compounds. Evaluation is made in each case by combing survivingfleas out of the animal's coat and comparing the number counted with thenumber of fleas in the control group and in the group treated withnitenpyram.

The procedure in detail is as follows: each cat is infested with 100fleas immediately after treatment on day 0. On day +1, each animal iscombed and the number of surviving fleas is determined; the survivingfleas are then replaced on the same cat and after 24 hours the combingand evaluation are repeated. The fleas still surviving after those 24hours are not returned to the cat. The described procedure is thenrepeated on days +3, +7, +9, +14, +21, +28, +35, +42, +49, +56 and +63and in this way the effectiveness and duration action are determined.The effectiveness is determined in accordance with the followingformula: ${\% \quad {effectiveness}} = {\frac{\begin{matrix}{{number}\quad {of}\quad {living}\quad {fleas}} \\{{on}\quad {the}\quad {control}\quad {animal}}\end{matrix}\quad {minus}\quad \begin{matrix}{{number}\quad {of}\quad {living}\quad {fleas}} \\{{on}\quad {the}\quad {test}\quad {animal}}\end{matrix}}{{number}\quad {of}\quad {living}\quad {fleas}\quad {on}\quad {the}\quad {control}\quad {animal}} \times 100}$

It is shown that the compounds of formula (I) according to the inventionachieve excellent long-term action. Very good action is obtained, e.g.,with Compound Nos. 1.001, 1.008, 1.011, 1.012, 1.013, 1.014, 1.015,1.018, 1.020, 1.021 and 1.022. An especially high level of long-termactivity is exhibited by Compound Nos. 1.008, 1.011 and 1.012. Fullaction (100% effectiveness) is observed over a period of at least 7weeks and after 7 weeks the action gradually declines to 26%. Incomparison, nitenpyram exhibits full action (100% effectiveness) onlyfor a maximum of 3 weeks. In a further, fully analogous test, CompoundNos. 1.019, 1.056, 1.057 and 1.058 also exhibit a long-term actionequally as excellent as the compounds mentioned above.

In dogs the test proceeds in an entirely analogous manner. In order toinvestigate the total action and any side-effects after administrationin the form of a pour-on formulation, Compound No. 1.008 is selected andtested on 11 dogs. The test protocol and the results are given inExample 7.

Example 7 Control of Adult Fleas in Dogs by Means of Pour-On Applicationwith Compound No. 1.008 of Table 1

Test protocol for each test compound: in order to determine theeffectiveness of the test compounds against fully grown fleas, threegroups each of three dogs (1 male and 2 female beagles) are used; onegroup consists of two dogs (2 male beagles) and serves as control group.The entire test group consists of 11 beagles between 1 and 3.5 years ofage. Each dog is infested with a total of 100 dog fleas [Ctenocephalidescanis], 50 male and 50 female. Group 1 is treated with 2 mg, group 2with 10 mg and group 3 with 20 mg of active ingredient per kg bodyweight. The treatment is effected by applying the pour-on formulation toa locally limited area on the back of the dog's neck. The fourth groupis the control group. The latter is infested with fleas but is treatedonly with a placebo, that is to say a formulation without activeingredient, and serves for control purposes. Evaluation is made in eachcase by combing surviving fleas out of the animal's coat and comparingthe number counted with the number of fleas in the control group. Theprocedure in detail is as follows: after treatment with the testformulation (day 0) each dog is infested on each of the subsequent days+1, +7, +14, +23, +28, +35, +49, +56, +63, +70, +77, +84 and +98 with100 fleas. On the following day, each animal is combed and the number ofsurviving fleas is determined. The surviving fleas are then replaced onthe same dog and after 24 hours the combing and evaluation are repeated.The fleas still surviving after those further 24 hours (2^(nd) day afterinfestation with 100 fleas) are not returned to the dog. Then on days+3, +7, +9, +14, +21, +28, +35, +42 etc. the described procedure isrepeated and in this way the effectiveness and the duration of actionare determined. The effectiveness is determined using the formula givenin Example 6.

Seventy-nine days after application of the pour-on formulation, the testcompound exhibits 100% action; it is still 98.6% effective on day 86 andeven on day 98 it continues to be 92.3% effective. Whereas the dogs fromthe three test groups exhibit no skin irritation or any otherundesirable side effects, the two dogs in the control group have to beremoved from the test program on day 84, because they exhibit seriousallergy symptoms and skin irritation as a result of the numerous fleabites.

Corresponding effects are also observed when the substances areadministered not in pour-on form but in the form of an injectionsolution.

Example 8 Control of Adult Fleas in Cats by Means of SubcutaneousInjection

Test protocol for each test compound: in order to determine theeffectiveness of the test compounds against fully grown fleas, fourgroups each of two cats from 1.5-4 years of age are used. Each cat isinfested with 100 cat fleas [Ctenocephalides felis (Bouche)]. Two groupsare treated with 20 mg of active ingredient per kg body weight. Thetreatment is effected by subcutaneous injection of a solution of theactive ingredient behind the left shoulder blade. While one group isinfested with fleas but is treated only with a placebo, that is to say aformulation without active ingredient, and serves as control, anothergroup is treated with nitenpyram as comparison substance. Evaluation ismade in each case by combing surviving fleas out of the animal's coatand comparing the number counted with the number of fleas in the controlgroup and in the group treated with nitenpyram. The procedure in detailis as follows: each cat is infested with 100 fleas immediately aftertreatment on day 0. On day +1, each animal is combed and the number ofsurviving fleas is determined; the surviving fleas are then replaced onthe same cat and after 24 hours the combing and evaluation are repeated.The fleas still surviving after those 24 hours are not returned to thecat. The described procedure is then repeated on days +3, +7, +9, +14,+21 and +28 and in this way the effectiveness and duration of action isdetermined. The effectiveness is determined using the same formula as inthe preceding Example.

It is found that the compounds of formula (I) according to the inventionachieve excellent long-term action after subcutaneous injection. Verygood action is achieved, e.g., with Compound Nos. 1.001, 1.008, 1.011,1.012, 1.013, 1.014, 1.015, 1.018, 1.020, 1.021 and 1.022. An especiallyhigh level of long-term activity is exhibited by Compound No. 1.012.

Full action is observed for a period of at least 20 days in comparisonwith 2 days in the case of nitenpyram. The analogous test with dogsleads to absolutely comparable results.

Compound Nos. 1.059-1.087 also exhibit very similar results to thosedescribed in Examples 6-8.

What is claimed is:
 1. A compound of formula (I);

wherein R₁ is hydrogen or a radical from the group C₁-C₄alkyl, formyl,C₁-C₆alkylcarbonyl, C₁-C₄alkylsulfonyl, aryl, arylsulfonyl,arylcarbonyl, heterocyclyl whereby said heterocyclyl is selected fromthe group consisting of dioxolanyl, pyrrolidinyl, piperidinyl,morpholinyl, pyrrolyl, furyl, thienyl, imidazolyl, tetrahydrofuryl,tetrahydropyranyl, dihydrofuryl, dihydropyranyl, isoxazolyl, oxazolyl,thiazolyl, oxazolinyl, oxazolidinyl, imidazolinyl, imidazolidinyl anddioxanyl, and C₁-C₆alkyl substituted with said heterocyclyl, whereby theheterocyclyl moiety is unsubstituted or mono- or poly-substituted byidentical or different substituents; the said substituents beingC₁-C₄alkyl, C₁-C₄alkoxy, C₁-C₄alkylthio, C₁-C₄haloalkyl, halogen,hydroxy, cyano, nitro, amino, C₁-C₄alkylamino, C₁-C₄alkyl)₂amino,alkoxycarbonyl, C₁-C₄alkylsulfonyl and arylsulfonyl; X is CH or N; Y isan electron-withdrawing radical, selected from the group consisting ofcyano, nitro and C₁-C₆haloalkyl-carbonyl; T and U together form aC₁-C₄alkylene bridge which is unsubstituted or substituted by a radicalR₁, or T and U together with the group —N—C—N— form a saturated orunsaturated 5- or 6-membered heterocyclic ring which may in additioncontain as further hetero atom O or S or the hetero group—N(C₁-C₆alkyl)-; R₂ is hydrogen or C₁-C₆alkyl; R₂′ is hydrogen orC₁-C₆alkyl; and R is C₁-C₂₀alkyl, C₂-C₂₀alkenyl, C₂-C₆alkynyl orheterocyclyl, each of those radicals being unsubstituted or substitutedby one or more identical or different substituents, the saidsubstituents being selected from the group halogen, cyano, nitro,hydroxy, C₁-C₆alkoxy, C₁-C₆alkylthio, C₁-C₆haloalkyl, C₁-C₆haloalkoxyand phenyl; whereby heterocyclyl is selected from the group consistingof dioxolanyl, pyrrolidinyl, piperidinyl, morpholinyl, pyrrolyl, furyl,thienyl, imidazolyl, tetrahydrofuryl, tetrahydropyranyl, dihydrofuryl,dihydropyranyl, isoxazolyl, oxazolyl, thiazolyl, oxazolinyl,oxazolidinyl, imidazolinyl, imidazolidinyl and dioxanyl; or isC₃-C₇cycloalkyl that is unsubstituted or mono- or poly-substituted byidentical or different substituents selected from halogen, cyano, nitro,hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₁-C₆alkoxy,C₁-C₆alkylthio, C₁-C₆haloalkyl, C₁-C₂₀haloalkoxy and phenyl; whereineach phenyl moiety is itself unsubstituted or mono- or poly-substitutedby identical or different substituents selected from halogen, cyano,nitro, hydroxy, C₁-C₆alkyl, C₁-C₆alkoxy, C₁-C₆alkylthio, C₁-C₆haloalkyland C₁-C₂₀haloalkoxy; or is phenyl phenoxyphenyl each of which isunsubstituted or mono- or poly-substituted by identical or differentsubstituents selected from halogen, cyano, nitro, hydroxy, C₁-C₆alkyl,C₁-C₆alkoxy, C₁-C₆alkylthio, C₁-C₆haloalkyl and C₁-C₂₀haloalkoxy.
 2. Acompound of formula (I) according to claim 1, wherein R₁ is —CH₂-Het; Xis CH; Y is NO₂; Het is heterocyclyl selected from the group consistingof dioxolanyl, pyrrolidinyl, piperidinyl, morpholinyl, pyrrolyl, furyl,thienyl, imidazolyl, tetrahydrofuryl, tetrahydropyranyl, dihydrofuryl,dihydropyranyl, isoxazolyl, oxazolyl, thiazolyl, oxazolinyl,oxazolidinyl, imidazolinyl, imidazolidinyl and dioxanyl that isunsubstituted or mono- or poly-substituted by identical or differentsubstituents; the substituents being C₁-C₄alkyl, C₁-C₄alkoxy,C₁-C₄alkylthio, C₁-C₄haloalkyl, halogen, hydroxy, cyano, nitro, amino,C₁-C₄alkylamino, C₁-C₄alkyl₂amino, alkoxycarbonyl, C₁-C₄alkylsulfonyland arylsulfonyl; T and U together form a C₁-C₄alkylene bridge which isunsubstituted or substituted by a radical selected from the groupC₁-C₄alkyl, formyl, C₁-C₆alkylcarbonyl, C₁-C₄alkylsulfonyl, aryl,arylsulfonyl, arylcarbonyl, heterocyclyl and heterocyclyl-substitutedC₁-C₆alkyl; each radical from the said group itself being unsubstitutedor substituted by C₁-C₄alkyl, C₁-C₄alkoxy, C₁-C₄haloalkyl, halogen,hydroxy, cyano, nitro, amino, C₁-C₄alkylamino, C₁-C₄alkyl₂amino,C₁-C₄alkylsulfonyl or arylsulfonyl; or T and U together with the group—N—C—N— form a saturated or unsaturated 5- or 6-membered heterocyclicring which may in addition contain as further hetero atom O or S or thehetero group —N(C₁-C₆alkyl)—; and R₂, R₂′ and R are as defined inclaim
 1. 3. A compound according to claim 1, which is a compound offormula (Xl):

wherein Hal is halogen; X is CH or N; Y is an electron-withdrawingradical, selected from the group consisting of cyano, nitro andC₁-C₆haloalkyl-carbonyl; T together with U forms a C₁-C₄alkylene bridge,which is unsubstituted or substituted by methyl or ethyl; and R₂ R₂′ andR are as defined in claim
 1. 4. A compound according to claim 1, whichis a compound of formula (XII):

wherein Hal is halogen, X is CH or N; Y is an electron-withdrawingradical, selected from the group consisting of cyano, nitroC₁-C₆haloalkyl-carbonyl; T together with U forms one of the groups—CH₂—CH₂—, —CH₂—CH₂—CH₂—, —CH₂—O—CH₂— and —CH₂—N(CH₃)—CH₂—, wherein allmethylene groups are unsubstituted or one of said methylen groups issubstituted by methyl or ethyl; and R₂, R₂′ and R are as defined inclaim
 1. 5. A compound of formula (I) according to claim 1, wherein R′₂and R₂ are each independently of the other hydrogen, methyl or ethyl. 6.A compound of formula (I) according to claim 1, wherein heterocyclyl inR₁ is pyridyl, thiazolyl or tetrahydrofuryl that is unsubstituted ormono- or di-substituted by halogen.
 7. A compound of formula (I)according to claim 1, wherein heterocyclyl in R₁ is5,6-dichloro-pyridin-3-yl, 6-chloro-pyridin-3-yl, 2-chlorothiazol-5-ylor tetrahydrofuran-3-yl.
 8. A parasiticidal composition comprising acompound of formula (I) according to claim 1 and at least onephysiologically tolerable carrier.
 9. A parasiticidal compositionaccording to claim 8, comprising from 0.1-99% by weight of a compound offormula (I) according to claim 1 and from 99.9-1% by weight of a solidor liquid, physiologically tolerable carrier, including from 0-25% byweight of a non-toxic dispersant.
 10. A parasiticidal compositionaccording to claim 8, which is a pour-on or spot-on formulation.
 11. Amethod of controlling parasites on warm-blooded animals, which comprisesadministering to a warm-blooded animal a parasiticidally effectivecompound of formula (I) according to claim
 1. 12. A method according toclaim 11, comprising the topical application of a compound of formula(I) according to claim
 1. 13. A method according to claim 11, wherein acompound of formula (I) according to claim 1 is administered in a doseof from 0.01-800 mg/kg body weight, based on the host animal.
 14. Aveterinary medicinal preparation against parasites comprising a compoundof claim 1.